The question you need to answer for yourself is how important is the "easy trailering"? And the trade-offs from sailing ability for trailerability?
Mast raising and how high the boat sits above the ground have a lot to do with how easy a boat is to trailer. I've always had trailerable sailboats, ranging from Sunfish/Laser to an ODay 25 to my current ODay (Stuart) Mariner (19ft). In some ways, the Mariner is the best at trailerability, in some ways it still is not great. The Sunfish and Laser are fun single handers, and trailer easy - but are difficult to launch/retrieve, rig and unrig without somebody else around to help. They also require a pretty agile person to sail in any kind of variable winds (typical on lakes).
My Mariner is pretty easy to single hand in my old age due to stability - you don't have to be on and off the rail all the time. The board fully retracts into the hull so is easy to launch in shallow water and only draws 10" board up. BUT it will skid sideways with the wind without at least 6" of cb down. The other issue for single handing is figuring out ways not to have to go up on the foredeck. On the Mariner, the mast can be easily reached from the cabin with the hatch open - which makes halyards pretty easy to reach. Jib sheets go to the aft edge of the coach roof on swivel cam cleats to easily manage from cockpit. No winches needed for standard jib. Mid boom mainsheet goes to centerboard trunk with no traveler to trip over. So a vang, tiller extension, and a tiller clutch are really the only non-standard tools needed for single handing. Mariner mast raising takes rigging a gin pole and some side-to-side stabilization as the mast goes up and down (I use rope baby stays), which adds time at the ramp. But mast raising is very simple and quick if there are 2 people instead of one.
I use the Mariner as an example of things to be considered for single handing, solo rigging, and solo launching/retrieving. My Mariner is not a quick launch if I'm single handed - I would not use it for solo trailered daysailing. But the 10" draft with fully retractable CB (and kick-up rudder) makes it fun to beach. The 3/4 sloop rig makes it a good and fun sailor. With an easily reefed main, I can enjoy 5-20 knots of wind. A local Sun Cat struggles at either end of the Mariner wind range, yet still has a 6" keel/CB stub that makes beaching awkward. But rigging/derigging is much faster.
Matching the trailer to the boat is important on a boat like the Mariner without a keel stub. If the trailer has the wheels outside the hull (mine does), the boat can sit low between the wheels, making for easy launching at shallow ramps, and built-in ladder if the wheel fenders are sturdy enough.
Think carefully about how you will actually use the boat - the trade-offs become more significant in the smaller boats.
Fred W
Stuart Mariner 19 #4133 Sweet P
Yeopim Creek, Albemarle Sound, NC
