Looks like you revived an old thread.
I wouldn't call a 26 footer a trailer sailor. I guess if one was set-up specifically for it you could get by but thats a huge boat to be trailering.
I ued to have a Starwind 19 that was the perfect trailer sailor. I could step the mast by myself without anything fancy or extra rigging. Something like that would be perfect for a first boat.
I just bought a 23 footer and I wouldn't consider it a trailer sailor by no means. Sure I might get a trailer and take a trip once a year to the keys but that just makes it trailerable. I still own a 27 footer I'm tryinng to sell, no way would I even consider putting that thing on a trailer.
hey look my santana 27 lives on a trailer when the sails arent flying and its going to see alot of trips to cal and mexico next year so it all depends on you not the boat. WDSchock builds a 40' that is trailerable ( legally) and its in a class by itself