Started with a TT. Then another TT. Then a 5er toy hauler. Then my present TT toy hauler.
No regrets at all. We just listed the Work & Play for sale on craigslist because I've decided to retire from the racing. We'll probably get another 5er just because we want something much bigger. But if we were looking to stay in the 30' range, I wouldn't have any problem sticking with another TT.
As scbwr said, a good WD hitch works wonders. I can tow my Work & Play as good as any 5er out there and I can back it into pretty much any campground spot.