Realistically you can probably trailer something like an F31 without special trailers or tow vehicles. Something like a Telstar 28 or a Contour are also options, but they are far less common. You could possibly include an F36, buy unless you have professional driving skills and a specialized trailer they are not a realistic option.
As a rule
multihulls can not carry as much as monohulls, but they tend to be faster which means less time spent on a passage
so you may not need to carry as much. There are plans for several other boats if you want to try and build yourself a tri you can tow. A rule
of thumb is up to around 35 feet a tri will have more room than a cat and be faster as well, larger than that a cat will probably have more room. The F31 and Telstar will run around $US100k more or less, the F36 $US150k or more. A Dragonfly is also a consideration, but they are few and far between.
Some of your other questions require more than a personal than general answer. Boats like an F31 or Telstar 28 have crossed oceans and cruised for months. People live aboard much smaller boats in marians; on the other hand some folks would say any boat is too small to live aboard.
Your best bet would be to try and find an Fboat you can hitch a ride on and see if you think it has the room for you to cruise
or live on. There are lots of Fboats around and the owners are not shy about giving rides. The other tris are much less commonly found for sale