Re: whats the largest trailer-able boat available- cruiser style
Generally, trailering a boat with more than 8.5' of beam will require a permit (you can get per-trip or annual). Much larger issue is the tow vehicle... anything above 25' will usually require an F150 class truck (or better) with full tow package. That, plus the pure hassle of driving such a large trailer\boat around -- and finding good spots to launch -- makes it pretty difficult in most areas. Gas costs money, too.
You'll need to think carefully about your usage pattern, availability of water \ marinas nearby, and the expense (and hassle) you're willing to take on. Forget trailering a bridge boat, and even a radar arch can force you to be very careful with your routes.
For me there is no question... my boat gets moved by the boat-man when necessary, and it sits in my slip for the season. This allows me to use it MUCH more frequently than I could ever do if it were on a trailer. It's WAY CHEAPER too (vs. maintaining a tow vehicle, permits, trailer, registration, insurance, etc.).
Virtually nobody trailers a large boat on a regular basis.
Forgive the question, but do you have any experience with boats, trailering, etc.? It's hard to tell from your post, but you seem sorta new to boating in general. Starting out with that size boat (potentially on a trailer) is a big step.