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.