Ok, I'll jump in here.
Towing is the easy part.
First let me say that all trailer boat are not trailer launchable (?). Some very nice fixed keel boats in the 25 to 29 foot area have trailers and can be towed but must be removed and launched with slings.
Second are the ones that use a tounge extension to get them deep enuff to launch. The problem with these is that sometimes the trailer runs off the end of the ramp before the boat launches. If that does not bother you than think of how you are going to the the boat and trailer back up over that lip. Don't forget about the other problems that arise from trying to put a boat on the trailer in 5 feet of water.
I have a Macgregor 25. Not bad but has a lot of drawbacks. Mainly no storage, it's taken up by a lot of foam. It will however launch in 2 feet of water meaning that I can launch it anywhere a ski boat can. It has a 700 pound swing keel that I have to lug around all the time when trailering.
My favorite would be one of the macGregor 26 classics wich are the 26d(dagger board) or the 26s(swing keel).
Both of the classics are water ballested so you dont have to carry about 1200 pounds around with you. You just have to open a valve and let the water flow in and you can blow it out before you put it back on the trailer. The best part is you can get into some lakes that just have a road leading down to them. The floation was moved to non storage areas and they have a queen sized berth under the cockpit. A pop top gets you some head room when at anchor.
A 10 hp outboard will get you to hull speed at 1/2 throttle.
They are easy to rigg--just undo the forestay all the rest stay connected so if you want to see what is on the other side of that bridge--go for it. Want to beach it on that sandy beach--pull up that under carrage and kick up the rudder and go for it.
If you want you can slip in a marina for the season and then put it in you driveway in the off season for maintence for free.