Is your driveway paved and close to level? If so, maneuvering the trailer using the dolly wheel on the tongue jack should be easy. Since you are starting with the TM wheels inside the garage and on a level floor, you are not moving the weight of the trailer up or down hill. The only thing you are pushing up and downhill is the tongue weight, perhaps 400 pounds. And although 400 pounds sounds like a lot, if you are rolling it up or down a very gentle slope, it is surprisingly easy.
My garage floor is level, my driveway is concrete and slightly sloped (down as you leave the garage), and this works for me. It isn't fast, but it works. However, my garage has very little fore-and-aft clearance, and I was bashing the drywall at the back. To prevent this, I bolted a 2x8 plank to the rear wall at bumper height. It absorbs the shock better than drywall (what doesn't?), and at the speed in question, doesn't hurt the TM at all.
Bill
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