"Do you usually float your BC and hand it up?"
It is not hard at all, gear up on the boat and roll in. Getting back in you have a few tether lines maybe with a ball float and clip hooks. Pull your BC off and hook it to the tether line and swim up to the stern. The tether lines can be hung from the sides as well as from the stern. Always make sure you also have a trailing line, at least I do. Most boats that are meant for offshore in the size you mention are outboards. These usually have a swim platform on one side or the other or both. Once your BC is hooked to the tether just walk up the swim ladder.
The towing thing aside, I have towed those huge camp trailers, not fun and they are meant for towing, each to their own, since having owned such a boat (26 feet) when I lived in Houston I have decided what can be done and what I want to do are two different things, certainly many vehicles today can pull those loads, I would go diesel. The mileage will be much better and having a vehicle that is up to the task will make it all go easier and most salt water marinas have boat lifts that can put your boat in and out of the water without backing your truck and trailer into the salt water. This can run anywhere from free to as much as 50 dollars.
My Merc 150 burns upwards of 6 to 10 GPH and at 26 MPH cruise it gets almost 3 miles per gallon!!!, twin 200 would probably consume 15 to 25 per hour. Yahooooo, burn that gas!!!!!!
Since you asked about getting in and out the BW does make dive specific boats. Go to their commercial division and you see that they have at least three boats in which a cutout is made in the side with a flip down ladder. Once at the dive site, the cutout pops out, ladder swings down and you step in and out of the boat fully geared up. Since the BW is fullly foam cored there is no danger of sinking. These are available I think from 17 to 24 feet--I could be wrong about that but might be worth your look see. I don't think they have a cuddy version though, to bad.
"will easily run you $50k to $125k."
Well, a BW in that size range, 26 feet BW Outrage is going to be a bit more than that new, the EastPort 21 with cuddy and single 200 horse Merc will be about 50,000 plus trailer etc. If you choose a used boat have it surveyed. Since the hurricanes already I notice some "repaired" boats showing up here in the Heartland that are obviously not from a local lake as they have Florida registrations still visible. Some of these could be a great deal, some not. I don't think there is a BoatFacts like CarFacts. One thing, you may already know, the computers on most any newer outboard can be read by any well equiped service tech giving you all sorts of info on the health of the engine(s), important if buying used.
Well, good luck, hope you find what you are looking for. Hey, here is an old picture, things have come a long way huh? N