Starter boat shopping questions.

[Riperoo]

ey all, poking around the idea of picking up a small boat, starter boat per se, I have a place in Cape May NJ and would like to get out and explore the bays, crabbing, some fishing, really like to try some fly fishing in the back bays, like something small, 16 to 20 max, trailerable, if it can fit in my garage in the winter, that would be a big bonus. The gamut of used out there is pretty overwhelming. Like to get any and all input on suggestions. Background on me, approaching retirement age, never owned other than canoes and kayaks, been on charter boats and rentals, so been exposed, but don't even consider myself an amatauer. Like to be around the $10k level, unless you all tell me that going new is the way to go. Like to hear anything, good and bad, don't pull any punches, the good, the bad and the ugly!!! TIA