You don't says anything about the vehicle you are using which would be good to know. That said, I had a 16ft hyside that I transported in a Jeep Cherokee for about 5 seasons. No problem.
Hypalon boats are good for that type of deal and as long as you don't do sloppy taco rolls before and after trips then they will get smaller than you'd think.
Get a good roof rack for the frame and be ready to strap dry bags up there when you've got other folks in the truck.
Sounds like you are already a lightweight packer so that helps.
Big trucks vs. a Prius helps allot, of course. I've migrated towards Suburbans these days as they are comfortable people and roomy gear haulers. Even with 3 people and a cooler, nothing needs to up top beside the frame and shitter( for obvious reasons other than space).
I completely get why folks trailer but doubt I ever will. A little organization, a good sized truck, hypalon raft and practice...not a big deal. Makes life easier for those frequent 4wd access points, too.
A well practiced guy with a trailer is always going to be faster than a well practiced guy rigging ground up. That said, can't tell you how many times I've been on the water faster than folks with trailers, too.
Less crap and a good system works wonders. Good luck with it.