Can't quite visualize what the location looks like. A photo might have been nice.
Once, and only once so far, I needed to back our 29' TT into a site with a very tight almost 90 degree turn off the road. I backed part way in, then unhooked the TT, then re-aligned the truck & trailer and then was able to back nicely into place. Didn't re-engage the WDH spring bars for the sake of only a few feet backing up so didn't take all that long. The end result was a very nice waterfront view of the ocean. :)
I wouldn't bother with a dolly - too costly, too heavy and too bulky.