Might want to consider launch, rig and comfort too
If you plan to keep your boat mostly on the trailer, rigging before each sail, you might want to consider the time and ease of rigging and launching. Some boats like the Mac 26 can be rigged in less than 30 minutes after you get the routine down. Others need a lot longer and need lots of muscle or a crane. Look for a good design for mast raising, as this is the most physical part of rigging. An easily detachable rudder gets weight off the stern for towing.Launching is another consideration. At one end of the spectrum, you have water ballast boats without a keel that sit low on their trailers, and therefore require less water to float off the trailer. The other end might be a full keel that requires a sling lift. You might consider where you will be launching from most of the time, and think about the angle of the ramp and if you will be able to easily launch. Water ballast boats are initially tender, but the offsetting benefit is that you haul less weight down the road.There is a vast difference in the roominess of say a Hunter 260 and some of the older designs. Boarding after swimming is much easier with the "sugar scoop" designs. There is standing headroom on the 260 for most people. You can see that I am biased towards the 260 as I own one.All sailboats are a tradeoff. You might want to look at the average conditions of the areas where you want to sail and determine if you really need a heavy boat. Lots of areas have winds of 10-15 knots most of the time, and most of the trailerable boats love this wind speed range. One bit of advice: make sure you go through the rigging and launch with the owner of the boat you are looking at before you buy it. Compare that launch site with the one you will be using the most.Good luck,Bert