We've had two TT's and now have a 2 week old 5'er. After towing the TT's for 10-12,000 miles and only towing the 5'er for roughly a 1,000 miles. I will say the 5th wheel tows much easier. Absolutely now sway whether passing semi's or in strong side winds.
Now backing up is a different story. I could put our 31' TT anywhere on a dime. The 5th wheel is a little different and I just need more time. I've only backed it in to 2 camping spots and our driveway twice. Each time I had overdrove the truck and couldn't bring the 5'er back around. Had to drive forward and restart. I like the layout in a 5th wheel better as you generally get more room around the bed area. Also there's a ton of storage in the front. Our new 5'er is 3' shorter but has the same sq ft. Another nice thing is I'll be able to squeeze into some shorter spots as I'll be able to back the truck under the 5'er a little if needed.
Hitching and unhitching IMO is way faster. Before I would need to get the WD bars out, back up, hookup, raise the TT tongue, hook up bars, lower the TT's tongue, hook up chains and safety wire.
With the 5'er all I have to do is flip the safety latch, back in till the pins in the hitch, flip the safety latch, attach the safety brake wire and done. Literally takes 1/3 the time. I've only hitched up 3-4 times and each time I have to stand there for a bit because I'm so used to it taking longer:) A