I pull a 44.5' fifth wheel with a long bed 1 ton pickup. We're a very long rig. When we first started out, our length was pretty daunting and we were very limited. After years with this setup and many nights on the road, my wife and I don't get very nervous anymore. If we hadn't spent so many months on the road together in the past year, we would both still be sweating bullets driving around town and trying to get to camp.
I wouldn't recommend this setup to very many people because size totally matters, but experience and an incredible partner will solve a lot of the tense moments. On the other hand, our experience has also taught us which parts of town to avoid and which camps to cross off our list.
We also found that one of the smartest things you can do is get to camp early (not "early" check in, but early in the afternoon). Parking our rig in a fairly empty park is very different than parking with neighbors on both sides of you.
A couple months ago we got to a little county park on the coast and we got there late (just as the sun was setting). The place was packed already and we didn't have any maneuver room on either side of the road with people's bumpers crossing the lines etc. It took about twenty minutes for my wife and I to finally drop anchor and we couldn't have done it without so much practice. Practically everyone in that camp stopped by during the weekend to shake my hand and shake their heads and laugh. That's not relaxing though and it's really the opposite of why we camp. I hope we don't ever do that again.