I just moved up from a 24' TT to a 28' TT and I noticed a HUGE difference. I can't imagine adding another 10' to the length! Then again, my 28' barely fits on the side of my house, and it is a challenge pulling out and backing in from my relatively narrow subdivision street development. My first two trips with the 28' have been a challenge backing into the sites, also. The first site was short and barely fit the TT alone. The second site was tricky getting the TT in between trees.
That being said, I would love to have something that big to live in once it was on a site!