We went 3 yrs with a TT. Moved to a 5'er last year. Went 300 miles to get it. Never towed a 5'er before. While we had some chucking issues that have since been ironed out, the initial tow was easy. I actually found myself running 65-70mph on a short stretch. I normally tow in the 60-65 range, but the 5'er is a much more relaxing tow. Can't say exactly why, but it just feels better connected to the truck.
Another thing that my wife brought up this last week while we were camping was the fact that last year I had broke my right arm and how much easier it is to hitch up the 5'er compared to hooking up spring bars on a WDH. I suppose I could've done it one handed, or have her help. But hitching the 5'er up is so much easier.
My wife would've had a heck of a time putting the EQ bars on our last TT. She could very easily hitch up the 5'er with me directing her.
Another nice thing is when walking around the trailer and truck you don't have to step over the tongue to get to one side or the other.
The added ceiling height and the more convenient storage also make them a plus IMO.
Simple things you don't really notice till you get out and use one for awhile.
Backing up is still tricky and we've had ours for a year now. It's not more difficult, it's just different. 5'ers corner a little tighter but you get use to that. The height thing is something to get used to. If you just do RV parks then no biggie. We tend to do mostly forest service CG's and therefore have to watch for low branches more. Funny thing is I have more trouble getting out of my neighborhood than driving thru most CG's.