I did it, it was a PITA. The HOA did not allow overnight parking.
I took a utility trailer, removed the rear gate, axle and springs and installed 2-8" swivel casters on the front and 4 straight 8" casters on angle iron just behind the axle location. This put the deck at about 12" off the floor. (Note: I could put the springs and axle back on and still use as utility trailer)
After unloading and reloading the TC in the street, I used a SUV to connect the hitch and back it carefully into the garage. A drop hitch ball on the truck would work. It cleared by about 2" on each side and the fan dome by about 2' on top.
One issue was the length of the raised jacks. I had to remove the rear jacks so they would not scrape when elevating the hitch.
I also had to bridge the street gutter to keep from stressing things. Casters are not rubber tires and have little tolerance for uneven surfaces.
Another issue is you cannot raise the TC top in the garage if you have a standard garage door opener.
After a few times, I paid for outside storage until we moved.
Why they won't build garage doors 8' tall......:M.
Others have built custom dollies with casters or 8" tires. There also have been ones on tracks or pulled into the garage with a winch.
Don't unload directly on the sloping driveway-you may see your TC try to walk into the street all by itself :E
Hope this helps. Measure very carefully. Good Luck.
Rick
04 GMC 1500 4X4X4, 04 Sunlite SB