Chatham & Orleans Properties rent Friday to Friday during Summer Months

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About Us

History of Pretty Picky Properties

Jim and Karen started Pretty Picky Properties as a result of meeting a need they had themselves. After deciding to rent their prized cottage in Brewster, they became frustrated with the lackluster marketing and absence of on-site attention their property received from their conventional rental broker. So they did it themselves. They tapped Jim’s 35+ years of marketing and advertising experience and applied Karen’s personal relationship management skills, honed in 30+ years as an educator.

They began greeting arriving guests in person at their cottage. As good as their cleaning service was, they developed their own, separate check list of safety, presentation and detailing steps and diligently executed them every rental turnover day to thoroughly prepare the property for arriving guests. To this day, the Pretty Picky Property Prep Punch List remains a key added value in the company’s service mission.

Along the way, Karen and Jim also discovered how good it feels to personally welcome families to their long anticipated summer vacation. That good vibe motivated them to become licensed agents, then brokers, so they could create a new kind of rentals management company. In 2003, Pretty Picky Properties was founded, representing only select properties and serving owners and guests at a level unavailable before on the Cape.

Next

Meet The Team

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Jim Decker

Chairman, Co-Founder, Marketing Director, Board Member

Jim started Pretty Picky with his wife, Karen, in 2001, by renting their prized beachfront cottage in Brewster. Jim still owns his Connecticut advertising agency and brings his 40+ years of marketing experience to position and promote the Pretty Picky brand. Essentially the company “scribe,” Jim draws on his longstanding copywriter’s background to compose everything from Pretty Picky’s marketing communications to its website property descriptions, Insider newsletters, publicity releases – even the company’s annual New Year’s thank-you postcard to owners. He and Karen spend their summers at their home on Long Pond in Harwich. They have three grown children, including Pretty Picky CEO, Blake, and five grandchildren ranging in age from teens to twenties. As his schedule permits, Jim enjoys throwing batting practice for his beloved Brewster Whitecaps and caroling with the Brewster Baptist Church.
• Ocean or pool?  Ocean
• Favorite Cape Beach? Brewster Dunes
• Favorite ice cream place? JT’s
• Favorite Local Restaurant? Brewster Inn and Chowder House
• Favorite Cape league team? Brewster Whitecaps

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Karen Decker

Co-Founder, Vacation Planner, Accounting Assistant, Board Member

Karen and her husband, Jim, started Pretty Picky in 2001 by renting their prized beachfront cottage in Brewster. Her 30+ years as an educator have sharpened her natural flair for positive relationship management, an invaluable skill in helping vacationers plan their family summer vacations. Guests are drawn to her trustworthy transparency, as she clearly goes beyond the call to situate them in their ideal property. For Pretty Picky accounting, she sweats the details and has become accomplished at identifying, investigating and solving problems. Karen spent summers on the Cape growing up and has always loved its ocean and superb beaches. She likes hiking, reading and watching sports on TV wit her husband, Jim. They spend their summers at their home on Long Pond in Harwich. They have three grown children, including Pretty Picky CEO, Blake, and five grandchildren ranging in age from teens to twenties.
• Ocean or pool?  Ocean
• Favorite Cape Beach? Coast Guard Beach
• Favorite Local Restaurant? Idaho
• Favorite Cape league team? Brewster Whitecaps

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Blake Decker

CEO, Board Member

Except for his parents who founded the company, Blake was Pretty Picky’s first full-time employee back in 2006. Beyond the expected fiscal and management responsibilities of a CEO, Blake’s focus is new business development, for both rentals and sales. He’s been remarkably successful, despite his modest self-description as “occasionally useful.” While in college he first came to the Cape in 2001 for a summer job at Chatham Bars Inn, where he met Jessie, now his wife of twenty years. They live in Brewster with their two teen-age sons who, Blake says, “ . . . are occasionally seen in public with us.” Despite a chronically stuffed schedule, Blake makes it a point to attend his sons’ games and has even coached their teams in baseball and basketball. The boys work for Pretty Picky alongside Chairman and grandfather Jim Decker in the summer. Their favorite pastimes include grill cleaning, screen repairs and a pizza lunch every Saturday.
• Ocean or pool?  Yup
• Favorite Cape Beach? Bayside Beaches for Sunsets
• Favorite Ice Cream place? My Freezer.
• Favorite Local Restaurant?
In Season: Pearl in Wellfleet
Off Season: Encore Bistro & Bar
• Favorite Cape league team? Brewster Whitecaps

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Scott Cheyne (say it “Chain”)

COO, Board Member

Scott joined Pretty Picky in 2013 and soon grew into his current role as the Chief Operating Officer of the company. Scott and CEO Blake Decker work together closely and comprise Pretty Picky’s senior leadership team. A text book example of the “work hard/play hard” lifestyle, Scott’s tireless management approach impacts every aspect of the company, from operations to technology, marketing to finance. He is often the specifier of new procedures and tools leading to improved efficiency and bottom line growth. His uncanny ability to read and understand people stems from his years of experience in qualitative research, leading focus groups for big brand marketers. He and his wife, Patricia, love the Cape Cod vibe and relish their summers in Chatham, often in the company of a foster dog. Rare spare time is likely spent on Outer Beach with a bonfire and a cold beer. Two favorite Cape events are the Chatham Christmas Stroll and Oyster Fest in Wellfleet.
• Ocean or pool?  Pool for me – ocean is too cold!
• Favorite Cape Beach? Outer Beach Chatham
• Favorite Ice Cream place? Short N Sweet, Chatham or Ice Cream Café, Orleans t
• Favorite Local Restaurant? Too many to list but in Chatham we love Pates , Blue Fin Sushi , Impudent Oyster , and eDel Mar .
• Favorite Cape league team? Chatham Anglers , I can see the field from my office!

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Kris Ramsay

General Manager

Kris joined Pretty Picky in 2015 and quickly grew into the role of General Manager. His rare combination of organizational, leadership and relationship management skills and flat-out hustle, qualifies him to run the entire day to day operations of Pretty Picky Properties. Kris, assisted by Kiel Lombardozzi, manages the myriad details of recruiting, training and scheduling Detailers, Property Managers, Cleaners, Linens Service and much more. He does it all with tireless efficiency and a welcome sense of humor. More than respected, Kris is beloved by all who work with and for him. He “followed a girl to the Cape” who is now his wife, Anna, and the mother of their two young daughters, Ruby and Cora. The Ramsays live in Brewster, where they support an abundance of non-human dependents, including two dogs, Obie and Lewey; two cats, Butter and Cocoa; two frogs, Valentine and Sugar Cookie; one fish, Bubblegum Berry; and nine chickens, Rhonda, Stella, Scout, Poppy, Tilly, Marshmallow, Lucy, Lazy Daisy, and Eggatha. Building on his years of experience with the Orleans Conservation Trust, Kris gives back to the community with his volunteer positions as Board Member with the Association to Preserve Cape Cod and an advisor to the Friends of Pleasant Bay.

• Ocean or pool? Pond! Then Ocean, then Pool.
• Favorite Ice Cream Place? Schoolhouse Ice Cream
• Favorite Cape Beach? Crosby Landing Beach.
• Favorite Local Restaurant? Hot Stove Saloon
• Favorite Cape league team? Brewster White Caps!

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Kiel Lombardozzi

Assistant General Manager

Kiel started as a property manager with Pretty Picky in 2019. He quickly advanced to become General Manager Kris Ramsay’s right hand man as Assistant General Manager. In that role, he schedules and deploys property managers as well as handling related owner and guest communications. A Cape Cod native, he married his high school sweetheart, Kerrie, and has two little girls, Nora and Maggie , as well as the family dog, Penny (7). A summer day off will probably find him boating or beaching with his family. He’s a big fan of Love, Live, Local Fest to support local Cape arts and crafts people and the small businesses that sell their wares.
• Ocean or pool?  Ocean (bayside)
• Favorite Cape Beach? Crowes Pasture ORV
• Favorite Ice Cream place? Ice Cream Smuggler , Dennis
• Favorite Local Restaurant? Hot Stove , Harwich
• Favorite Cape league team? Yarmouth Dennis Red Sox

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Stephanie Kalis

Vacation Planner, Marketing Coordinator

Stephanie joined Pretty Picky in 2018 as a Detailer. She has since grown into the double role of Vacation Planner and Marketing Associate. As a Vacation Planner, she works tirelessly to find the perfect property for each inquiring family seeking an unforgettable Cape Cod vacation. In her marketing role, she manages the company’s direct marketing via Constant Contact, designs and produces local advertising, and serves as webmaster for prettypicky.com. A Cape “Wash-a-Shore,” she met a guy who told her it doesn’t snow on Cape Cod. She married him and moved to the Cape, which was buried under 30+ inches of snow that year. She and husband Martin live in Marstons Mills, have four grown children, two grandkids and the world’s most laid-back canine, Grady. When not working you can find her clamming or watching a cape league game.
• Ocean or pool?  Pool
• Favorite Cape Beach? Dowses Beach in Osterville
• Favorite Ice Cream place? Jimmies and Steve & Sue’s
• Favorite Local Restaurant? ” The Ho” in Cotuit
• Favorite Cape league team? Cotuit Kettler

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Martin MacNeely

Vacation Planner, Property Manager

Martin wears many hats for Pretty Picky. He started as a part-time Detailer in 2018, then went full-time in January 2021 as a Property Manager and Vacation Planner. A retired Barnstable Firefighter, Martin also heads up Pretty Picky’s Guest Safety initiative , where his experience has proven invaluable. He came to call Cape Cod home when he was in high school and his parents retired and moved here. He says he “needed to follow the food and shelter.” Martin is married to Stephanie Kalis, another stalwart Pretty Picky team player, and they are parents of four children, two grandchildren and Grady, a Wheaton Terrier and the unofficial Pretty Picky mascot. For fun, Martin likes to watch Cape League and Boston Red Sox baseball, work in his yard, walk beaches and trails and drive around the Cape in his 1968 VW convertible bug.
• Ocean or pool?  Pool
• Favorite Cape Beach? Loop Beach
• Favorite Ice Cream place? Four Seas Ice Cream
• Favorite Local Restaurant? Villaggio Prime Bar and Grille
• Favorite Cape league team? Cotuit Kettlers

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Stephanie Marquis

Vacation Planner

Stephanie joined the Pretty Picky team in August 2022. She brings a thorough understanding of the Cape Cod vacation market, gleaned from several years as general manager of a beachfront inn in Harwich Port. Since coming on board with Pretty Picky, Stephanie has ambitiously made it a point to get to know the company’s rental portfolio, so she can intelligently respond to virtually any inquiry, focusing on her assigned properties. Stephanie also has a flair for design and color and has been helpful to owners and other vacation planners in making creative suggestions about furnishings and features. Born and raised in France, Stephanie came to Cape Cod out of a desire for travel and new experiences. Her warm weather diversions include walking, gardening and sun bathing. In the off-season, she gets into crafts and volunteering. She has a furry four-legged child named Pierre.
• Favorite Cape Beach? Skaket Beach in Orleans
• Favorite Ice Cream place? Sunday School in Harwich Port
• Favorite Local Restaurant? Rock Harbor Grill and Buca’s in Harwich

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Carla Hemmings

Vacation Planner

Carla started at Pretty Picky in May of 2023. A “Wash-Ashore” from San Diego, she married a Cape Cod native and moved to the Cape permanently in 2002, where she gained valuable experience in vacation rentals, property management and the Cape Cod market working for William Raveis and Gibson Sotheby’s International. As a Pretty Picky Vacation Planner, Hemmings manages reservations for her assigned properties and serves as the primary contact for owner and guest communications. She and her husband, Mike, built their beloved Cape Cod colonial home where they raised their two children. She and her family love the beautiful scenery, beaches, bike trails, sunsets, and historic sites which make up the region’s unique character. Time off will often find Carla reading, embroidering, visiting museums, art galleries or beaches. The family has a golden retriever and two marmalade cats.
• Ocean or pool?  Pool
• Favorite Cape Beach? Nauset Light Beach
• Favorite Ice Cream place? Schoolhouse, in Harwich Port
• Favorite Local Restaurant? Mahoney’s in Orleans and The Pearl in Wellfleet
• Favorite Cape league team? Orleans Fire Birds

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Kristen Bottiggi

Financial Controller

A more recent addition to the Pretty Picky team, Kristen joined the company in 2023. She brings three decades of accounting and management experience to her position as Financial Controller. She is a proven performer in total accounting management, experience gained mostly from 14 years with her former employer, Guaranteed Fresh Produce in Hyannis, MA. For Pretty Picky, Kristen oversees every aspect of accounting and financial management. Kristen is a native “Capie” and currently lives in Wellfleet with her fiancé. Her parents and brother all live on the Cape as well. On a day off, you may catch her enjoying the beach or out on the water in her boat. She also enjoys skiing and has been known to take a winter vacation to hit the slopes in Park City, Utah. As a Cape Cod native, she understands the challenges faced by local year round businesses and does her best to support them, especially in the slower off season.
• Ocean or pool? Both. Ocean is always #1
• Favorite Cape Beach? Jeremy Point
• Favorite Ice Cream place? Nauset Ice Cream
• Favorite Local Restaurant? PB Boulangerie

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Forrest Bartley

Accountant

Forrest has been a dependable, steady hand in accounting for Pretty Picky since 2021. He is a Cape Wash-a-Shore, as he likes to say, “I came to the Cape on vacation, found a job instead.” He has extended family living on the Cape as well. When he’s not managing spreadsheets for Pretty Picky, a warm summer day will likely find him sailing on Nantucket Sound. And in the off-season he’s all about kite surfing at West Dennis Beach.
• Ocean or pool?  Ocean
• Favorite Cape Beach? Harwich Port
• Favorite Ice Cream place? Sundae School 
• Favorite Local Restaurant? The Port Restaurant 
• Favorite Cape league team? Harwich Mariners

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Richard Jennings

Communications Coordinator

Richard came on board with Pretty Picky on September 1, 2023. He manages the phones for the company and in that role is often the first real time contact a new Guest or Owner has with Pretty Picky. Before joining the company, he honed his customer service and communications skills as a reservations agent for Ocean Edge Resort and Golf Club. His upbeat, helpful tone and manner, coupled with his excellent relationship management skills, make him the ideal first contact for telephone inquiries. A Cape Cod “Wash-a-Shore,” Richard grew up summering in Orleans and ultimately moved here full time to be close to family. His parents, sister, two nieces and a nephew all live on Cape, allowing him to spend as much time as possible with them. Richard enjoys life’s simple pleasures and is often known to drive to the beach and just gaze at the ocean.
• Ocean or pool?  Ocean
• Favorite Cape Beach? Nauset Beach
• Favorite Ice Cream place? Emack and Bolios
• Favorite Local Restaurant? Basco grill
• Favorite Cape league team? Orleans Fire Birds

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John Chrysogelos

Property Manager

As personable as he is talented, John is a favorite of Pretty Picky owners. He started with Pretty Picky in 2021. John can be accurately described as organized, resourceful, and caring. He is known for his creative “McGiver” approach to expediting solutions to property problems, ranging from non-working appliances to frustrating window treatments to dysfunctional gas grills. John’s presence on the Cape can be traced back to age six, when his family began vacationing here. Realizing a longstanding dream, he and his wife, Ellen, purchased a property and semi-retired here in 2021. He loves sailing, kayaking and the off-season when beaches and restaurants are less crowded.
• Ocean or pool?  What is a “pool” …. This IS Cape Cod
• Favorite Cape Beach? Skaket
• Favorite Ice Cream place? Ice Cream Café
• Favorite Local Restaurant? The Sparrow for morning coffee, 3 Fools, Corner Store, Rock Harbor Grill, Cape Sea Grille
• Favorite Cape league team? Orleans Firebirds

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Jeff Parker

Property Manager

Jeff began working with Pretty Picky in January 2023. It quickly became evident that he could be assigned virtually any task with complete confidence that he will produce a favorable outcome. The busier he is, the happier he is. He takes pride in his on-the-job efficiency. He describes himself as always “Ready to go.” Ready to go anywhere and take on any assignment. Jeff and his partner, Ruiz, have owned a house on the Cape for 10 years, having moved permanently from Boston three years ago. They have one spoiled cat named Elzinha (Hebrew for Paradise).
• Ocean or pool?  Ocean
• Favorite Cape Beach? Crosby Beach 
• Favorite Ice Cream place? Brewster Scoop
• Favorite Local Restaurant? Rock Harbor Grill
• Favorite Cape league team? Brewster Whitecaps

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Art Arnold

Property Manager

Art joined the Pretty Picky team in 2022 and quickly became a key go-to guy for whatever property needs come up. He describes himself in three words: “Love to help.” He is a retired senior manager in the software business who has lived and worked in three different countries. Art and his wife, Judy came to the Cape in 2005 when they purchased and ran a B&B in Brewster. He has been married for 45 years and is the father of two beautiful daughters. His favorite Cape Cod interests are sinking birdie putts and watching Cape Cod League baseball. When asked what he does in the off-season, he responded, “There’s an off-season?” Probably not, when you’re a Pretty Picky property manager.
• Ocean or pool?  Ocean
• Favorite Cape Beach? Breakwater
• Favorite Ice Cream place? Brewster Scoop
• Favorite Local Restaurant? Spinnaker
• Favorite Cape league team? Brewster Whitecaps

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Paul Freehauf

Property Manager

Paul signed on with Pretty Picky in 2022 and has been one of the company’s most valuable “go-to guys” ever since. He is consistently efficient, often addressing and resolving issues at more properties in less time than estimated by management. Paul describes himself as “almost native,” having been on the Cape for more than 50 years. His original reason for Cape relocation: it’s the opposite of New York City, from which he came. Paul spends his spare time working on his own house projects. In the off-season, he, his wife Carole and son Dylan are into hiking, clamming and grilling.
• Ocean or pool?  Ocean
• Favorite Cape Beach? Any on the Outer Cape.
• Favorite Ice Cream place? Four Seas
• Favorite Local Restaurant? The Pheasant in Dennis

Looking for Seasonal Work?

Nearly all the full-time staff featured above started as part-time seasonal employees. If you’re interested in joining the team as a seasonal Detailer, Linen Driver, or Property Manager,
please contact Kris Ramsay at 508-896-3241.

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