The challenge backing up a PUP vs a TT is not a PUP vs TT issue. The reason PUPs are harder to back up is because their wheel base is shorter than the TT wheel base you may consider.
I've had both a PUP and 3 different TT, each one got longer than the one before. By far, the "easiest" to back up is my now 35.5 foot TT. I still have a utility trailer with the same wheel base length as my original pop-up. And yes, with the same tow vehicle, the utility is much more of a challenge to back up than the 35 foot trailer, only because the sensitivity to any steering change is so fast with a shorter wheel base trailer.
So, what I'm saying is, if you can back up your pop-up with no problems, you'll find a longer wheel base trailer easier. The combination is.... the shorter the wheel base of the tow vehicle and the longer the wheel base of the trailer, the easier they are to back up. (This is proven over and over again when I hook up my utility trailer to my John Deere 735 mower-tractor and put it in places the truck navigation would be much more challenging).
Towing ALL depends upon your tow vehicle. If you are towing a TT with a small SUV, it will fail miserably towing a TT. But if you are already towing the pop-up with a 1 ton diesel dually, towing a TT will be non-mute.
We towed or pop-up originally with a Chevy Lumina Mini-Van. We had to go to a smaller pop-up to tow it comfortably, but it towed the pop-up for 6 years with no problems. Under the program "cash for clunkers" we ended up trading the mini-van for a used Suburban 1500. The air conditioning went out and they were wanting over $4000 to switch over to the non-freeon system. We said no, it wasn't worth it. We traded for the cash-for-clunkers program.
The Suburban towed the pop-up absolutely flawless. In fact, we got strange looks when we went to campgrounds because we were towing a smaller pop-up with a big vehicle! But when we decided to go from the pop-up to an 18 foot (lite) Dutchmen Sport, that Suburban towed for 3 months and then the transmission died. The engine had lots of power to pull, but the transmission did not! Little did we know.
We replaced with a new (rebuilt) transmission, and the Suburban handled towing even worse. A month later, we traded the Suburban for a Chevy 3500 dually (gas) one ton and never looked back towing again with anything else but one-tons. We've have 3 different 1 tons now, 1 gasser and 2 different diesels.
Whey did we trade the first one-ton? Dealer informed up the frame was rusting out and we were taking a risk towing a larger trailer(by now we had a 31 foot TT).
Second 1 ton had a fiberglass body. And although the transmission and engine were unbelievably magnificant, the body began to form spider cracks and the doors began to form rust from inside. We traded it and got $18,000 for it.
Now on our 3rd dually (got it brand new)... diesel Duramax 3500, the towing power is beyond amazing! We now have a 35.5 foot trailer, with carrier on the trailer hitch, our total length is 59.5 feet for the entire rig.
Towing is amazing! Except for turning intersections in town, our combination is wonderful. No problems backing up, towing, winds, semi trucks suck and pull, or anything. It tows marvelous in mountains, snow and ice, and flat land.
What I'm saying is, the success for a successful "tow" is to have a tow vehicle that is (literally) an over-kill for what you are needing to tow. If you do, you'll never experience any issues.
With 59.5 feet of "rig", I have no problems navigating almost anywhere. I do occasionally pass a fuel station if it's really a tight entry and exit. But there is almost always another one 1000 feet further down the road that will work just fine.
Campgrounds? we selectively choose our sites to make sure we can fit the space. Never had a problem getting into any campground or getting a spot. It might not be the most popular, desired spot, but that's usually because "that" spot is already taken. But we can get into any campground. We do primarily State Parks.
Hope this helps.