At some point, you have to say to yourself, "What can't I leave behind?" We hauled a sailboat (38' long on the trailer) behind a 40' motorcoach, and Joan drove separate with our SUV so we'd have a daily driver. We did that for a couple years, and it became a giant pain in the butt... too long to fit in most campgrounds and driving separate sucked.
When your RV is also your daily driver (as with a Class B, small motorhome, or truck camper), you have to unhook each time before you leave the site. Even if you don't mess with water and sewer each time, most of us want electricity at the site. That gets old after a while, too.
Getting enough towing capacity to handle a 25 or larger boat is another problem. Most Class A's have a 5,000 pound (or less) towing capacity, until you get into the bigger diesel pushers. The Earth Roamer and some of the new "Super Cs" are certainly capable of towing more, but then you are back to the "daily driver" situation, especially problematic when you stay in one place for a while.
We are not big on using the boat as our camper... it works fine when you are enroute to another great boating place, but it certainly isn't going to be a workable solution if you intend to stay in one place on land for a while. As I've mentioned before, we have run into RV parks that wouldn't allow us to stay in our boat.
I agree with Dusty, Bill & El, that the truck camper is the easiest "down the road" solution, especially if you are towing a 22. (Not a fan of the "beefed up" stinger-rods for towing a heavier load with the camper.)
Our solution: decide which is more important. Are you going to spend the season boating or RVing? If you want to go to the Sunbelt, park in a nice RV park, and enjoy the activities and the weather, a "livable size" RV is the best solution. 5th wheel or motorhome with a separate bedroom, bath, living area and kitchen will give you comfort while away from home. There is a LARGE community of full-time RVers and that is their only home. We did winters in the south in our coaches for a lot of years and really enjoyed that lifestyle.
If you are going to spend the season boating, get to where you want to be, put the truck and trailer in storage, and go cruising.
We are content with our small toy-hauler for our summer work situation, but it isn't what I'd want to spend the winter in if we were going to extensively RV. There are plenty of people who leave an RV in the south, have it hauled to storage, and drive their car or truck back north in the spring. That could certainly be a workable solution if you were going back to the same place each year, and you could still haul your boat back and forth.
At some point, you just have to choose how hard you want to work at traveling. I miss having Wild Blue with us, but we would have froze to death early on here at Yellowstone. Since I spend long days on the big boat, when we have time off, we are enjoying the land exploring (and the motorcycling). 3 1/2 months on one lake wouldn't be my idea of fun with our boat. However, there are plenty of folks here who are doing just that - and having a nice "cabin on the lake" for the price of a seasonal slip. I don't see many of those folks going out on their boats very often... but I wave at them while they are having drinks in their cockpit or up on the flybridge.
I don't consider our current situation "RVing"... and I am anxious to get back to Wild Blue and get her wet again.
Best wishes,
Jim