I am also a solo traveler. I find hitching up to my 5th wheel is really easy - all I do is look out the back window, but I do stop backing up about a foot away from the hitch to get out and make sure everything is lined up. Backing up into a campsite is no fun if there are any close obstacles. I just stop and get out real often during the process. If really worried, then just ask a neighbor help. But make sure to 'trust but verify' all suggestions and directions from others.
Pull-throughs make me happy.
I find it critical to map out the day's route, and any projected stops, the night before because there is little you can do to check the map when you are driving. You really need to have your ducks in a row when you pull onto the highway in the morning. Know where you are going and the route you are taking. I write down the campground name and phone number, along with the highway exit number on a piece of paper and have it handy in case I need to call them for any reason. Know the clearance for any bridge you will go under if not on the interstate and your clearance requirement is higher then about 9-10 feet. I also have a piece of paper with my clearance written on it and taped to the dash for quick reference.
My truck has a large built-in GPS but I also bought the Rand Mcnally and I mount that one on a RAM windshield mount. I angle it down so it rests right on the dash just above the Ford GPS so I can glance over and see them both. If possible, I input the same destination into both and set one on long range and one on short range. That way I'm reasonably certain of the route if they both provide the same directions. I know this is overkill, but I got the Rand mostly because it had additional RV-type features the Ford unit did not. I'm about to start full-timing so I'll be using it all the time.
And just FYI, I've had the RAM mounted to my windshield for about 4-5 months now and it has never once loosened up and fallen ! I've been using their products for many years - they make great stuff !
Tim