If you want to do it, you will do it. A smaller boat will get more use. The boats I've had always got more use when on the water, than on a trailer, (it always seems more trouble to launch for a few hours use than is worth it). I've had many weekends that were cut short because of job that the boat never moved, because by the time I could launch I would be worried about getting it back on the trailer. When in a slip, I could go out for an hour just to look around without worries.
Get a boat you can single hand, then you don't have to rely on "help" to get it out there.
The Sun has Risen on a New Day filled with the Promise of Adventure.