Yes, sometimes leveling my TT is a pain and no, most TTs have stabilizers that should not be used to level. Not sure if TT frames are strong enough to level with stabilizers. Winnebago’s are not and I wouldn’t try it. Hitching and unhitching is easy with the right attitude and a check list. Backing up improves with practice. By the end of a trip I’m an expert. With a truck you could carry extra fresh water. I’d be more concerned with waste tank capacity.
I much prefer my “tuff” big tow vehicle and TT to a C with a little toad. Park the TT and go exploring!