"Vehicle tracking is WAY different (each trailer cuts inside of the tow vihicle 8-10") so clearing corners are tricky!"
That is simply incorrect, as the rear of the fifth swings out on a turn, and the boat will follow almost in the same wheel tracks.
I towed a boat for years behind my old fifth with zero problems, pulled like a dream. But I wouldn't do it with the Flagstaff, as the frame is much lighter. Probably still ok, but I'm a little more fussy with our brand new camper.
Your Wildcat may have a heavier frame, but I would still not pull too heavy a boat. Someone posted the preferred ratio of weight as percentage of the camper weight, I think it was 1/3. So if your fifth is 9000 lbs, a 3000 lb boat would be ok.