Ive had to do similar jobs a BUNCH over the years, after much mud, sweat and tears we’ve come up with the best compromise.
Get the TV to the trailer on a different path, even if only by a few feet, than what you will use to get the trailer out. This means you’re not trying to tow out on a chewed up path.
Have to TV in the lowest possible gear / range available and have a tractor, any tractor pulling the TV by a very long cable or tow strap. Slow steady matching speeeds is the key. You’d be surprised how little extra pulling makes a big difference. Princess Auto has low priced ones, link several together.
On the tow out, don’t be concerned with a straight line, go around standing water wherever possible, even a small amount of water will mean tire tread clogging mud.