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.
Starwind 223 & Compac 16