Getting 50A to the TT is pretty do-able if you have the space for the larger breaker box. BUT, those outlets are still on the same circuits that run thru the trailer...the only way to avoid tripping breakers is to break up those circuits into more circuits, which involves running wire through the trailer, not just to the panel box.
Electronic devices are pretty low current draw so can't imagine that even all of the stuff you listed would draw more than 15A on one circuit.
Before you spend $$$ to re-wire the trailer, try using an aux cord. Run an extension from the 20A breaker on the pedestal to power the outside fridge, icemaker and awning lights. Keep the hot water heater on gas, not electric. Go through the trailer one breaker at a time and see which outlets are on the same circuits. You may be able to relocate a few key items to distribute the load better.
I would try the easy stuff first before you dive in and rewire the trailer.
