IMHO, I don't think a 5th wheel is difficult at all. We had been looking at 5th wheels and travel trailers for years and had only pulled a tent trailer once when our boys were young. That trip was almost 4,000 miles. 25 years later we decided to buy a tent trailer and after 5 trips decided it was too much work to set up and since we were planning a trip to Alaska, we knew that the tent trailer wouldn't cut it. So......we sold it and lost a few bucks. So all we had pulled to this point was a tent trailer.
Now, we start looking at 5th's and TT's again and quite frankly, a 5th is a bit imposing to look at because the front sits up so high. However.......the payback is a high ceiling and a separate bedroom area which we really love. And fear of pulling a large rig is only due to lack of experience. It took me all of about driving it home to be comfortable.
So now I'm hauling a 28' unit instead of a 14' tent trailer. Guess what? Pretty darn easy and as far as backing it up, it is easier than my tent trailer. Put it right in my driveway on a dime the first time I backed it up.
Safety wise, no white knuckle trips, no tail waging, no movement as big semi trucks pass me and I can have mine set up much quicker than our friends travel trailer. I give up space in the bed of the truck, but I don't need the space.
Cost for fixing stuff is no different than a travel trailer and heck, yes I could forget to drop the tailgate, but I could also forget to attach the emergency brake cable or connect the electric brake control or retract the front jacks or many other things. Just need to be careful and either have a check off list or double or triple check the rig before you hit the road.
My wife and I are pleased that we bought a well built 5th wheel. Would I have been happy with a travel trailer? Heck yes.......we just love to travel, but a 5th suits us just fine and most important, we both feel safe pulling it and the set up is 15 minutes.
Stan