You may also want to do research
on the fine line between "easily" trailered boats, and boats that technically are trailerable but not easily. For example, Bucaneer 18, Coronado 15, Hobie 16/18 cat, Nacra cat, Prindle cat, and many, many other 15 - 19 foot "planing hull" boats are light weight, extremely trailerable and have the advantage that you can pull them behind almost any vehicle, and actually travel on long vacation
trips and take your boat with you anywhere. The speed on some of these is GREAT!! but you will get wet so it can be a short season....I did that for a few years and it was a lot of fun to sail many different inland lakes as you travel...maybe not as much an option for you in Maine eh?
The next size up being "technically trailerable" but not all that easy because they are small keel
boats, like a Catalina
22 that weighs (help me out here friends) in the area of 3,000 pounds...GREAT boat for a new sailor, but not easy to trailer for a day trip at all. you can move a Catalina
22 behind a V8 vehicle but it would be a tough haul behind a V6. (I moved one up a high altitude canyon behind a 4 cylinder but would not recommend it)
Anything up from that size is a candidate to stay in the water
on a mooring
or in a marina...so as you get as many free rides from other sailors like mentioned above consider those 3 categories too.
One personal recommendation...don't buy a trailer sailer boat that is a "project boat"...you can nickel and dime yourself in repairs
into the price
of a only slightly used boat
...and if you do a trailer, get as big a tires as possible and GOOD bearings!
Go hop some free rides!!
If you were in Dallas area I'd invite you out and I bet others in your area would too...just have to find them