Sail a lot
One more vote for sailing on as many different kinds of boats as possible before you buy. As an experienced boater, you already know what you like and dislike about certain kinds of boats, and I am sure also know what kind of powerboat best suits you. However, you have yet to determine what kind of sailing you like, and what kind of sailboat suits you best. You mentioned a 30-35 footer maybe as something to look at. An Alberg 35 built in 1960 is a much different boat than a Catalina built in 1990. Completely different levels of comfort below, and they sail completely differently. Before you buy a sailboat, do some testing; figure out what is important to you, then you can choose a boat that fits you, rather than pull the trigger too quickly and be stuck with a boat that isn't suited to your desires.
One more vote for sailing on as many different kinds of boats as possible before you buy. As an experienced boater, you already know what you like and dislike about certain kinds of boats, and I am sure also know what kind of powerboat best suits you. However, you have yet to determine what kind of sailing you like, and what kind of sailboat suits you best. You mentioned a 30-35 footer maybe as something to look at. An Alberg 35 built in 1960 is a much different boat than a Catalina built in 1990. Completely different levels of comfort below, and they sail completely differently. Before you buy a sailboat, do some testing; figure out what is important to you, then you can choose a boat that fits you, rather than pull the trigger too quickly and be stuck with a boat that isn't suited to your desires.