Why not take it to a Marina and use the Travel lift, it could be a lot safer, less of a hassel and in doing this you have professional help with your rigging, a 27 foot boat mast isn't the easiest to just pop up on your boat at the ramp they are fairly heavy and I wouldn't do it with my girlfriend and nobody else. You also have to make sure that you don't put up your mast and then realize you have a bridge down the road and have to take it down, I don't know about up North but a lot of ramps down here in Florida are up smaller creeks and rivers which are crossed by low lying bridges that allow for small water craft generally on trailers but not sail boats with a 30 foot mast, know what I mean.
Oh I agree, a whole lot less hassle, but to me the reason to consider a boat trailerable is if you are able to take care of that yourself.
At more than a few yards up here, winter storage costs include launch and retrieval, and are about the same as launch/haulout and mast (un)stepping fees. So, if you don't plan on launching and stepping the mast yourself, you would be farther ahead to forget about the trailer. (driving distance to work on the boat could easily offset any savings though)