Ok, so you asked a sailing forum to decide between motor and sail boats? heheheh
Motorboat = boat goes fast, boat goes slow, turn wheel, boat goes fast, boat goes slow, oh no, motor no work... whoopsie!
Sailboat = Ok Vang on, backstay tighten, puff coming, point higher, ease off, speed up some, is the depth good this close to the island?, am I making better speed than x over water? If the wind picks up to 15 knots, what settings will I need? weather report says calm wind becoming 15-20... etc.
Yes sailing is very mental! It can be as simple, or as complicated as you like... add racing (even just for fun) to it, and it becomes a barage of variables to manipulate, and be manipulated by.
Enough of that... My decision was a Capri 22. My lake does not allow overnighting (I know dumb). However, my criteria was, keel, enough room for 2 to overnight, decent sailing performance, and about as big as I could easily get and still single handedly trailer, rig, and sail.
The capri is mostly a day sailor.... It DOES have a decent sized V-berth, and a porta pottie. You could also put a rail BBQ on it (I may depends). It sails like a dream, and I have the wing keel, so getting it on and off the trailer on a normal ramp for my RAM 2500 is easy enough, without much hoopla.
I second the Catalina 22, in that it is quick, plentiful, has nearly as many controls as my capri, sails decent, parts are cheap, and it it laid out a little better down below than mine (mine is just basically 2 berths and a V berth), the Cat 22 has a nice table/setee setup.
Cat 22 will run you anywhere from 1500 with a trailer in decent shape, to 4500 for boats around 20 years old. Capri's like mine, if you want slightly faster, can be had (again 15-20 years old) $3000-$6000.
Hope that helps.