We used to do what you are describing using manual labor. Grab a few of the neighbors and have them push from the rear of the TT (corners or bumper only) while I made sure the tongue jack with wheel attached went in the correct direction/spot.
To get the TT out I would have the neighbors push from the front.
It would take four plus me to get it where we needed it.
Beer was their reward...
A power dolly would be a better solution. Look for them on Craigslist. I see them list from time to time
Here's an extreme version https://losangeles.craigslist.org/sfv/for/5169543477.html
I've seen others that are much shorter and in the $300 range.
