Hi, Gypsy. I'm another vote for the hitch-buddy. I like mine so much that it never leaves my Jeep, even when I'm not towing. The last campout of the fall in 2009, other people at the campground watched me backing uphill and to left to hitch up my trailer on a site that was on a slight grade - and after I hitched up in one try, four neighbors borrowed the HitchBuddy for their own hookups (used on rigs from a small 15 foot popup to a ginormous 5th wheel.) Mine was a bit more than Arne's - I think it was $14.99 at Walmart. Worth twice that in saved time and frustration.
To your first question - what is the hardest thing to do alone?
Well - backing my Sunspot into my storage garage, which has a short roadway in front of the doors and is also slightly uphill, is kinda tricky for me. But I'm getting better. Plain old backing up into a site I practiced in an open parking lot aiming for a spot between two traffic cones until I could do it with a minimum of swearing and without taking out one of the cones.
I think the hardest part for me was getting practiced at not overpacking - the less I bring, the less of an issue it is to set up and tear down. So I work hard at paring down.
And in the paring down category, although I've themed out my Sunspot in vintage 70s Tupperware and other stuff, I decided that the first place I needed to pare down was my camp kitchen. When I pack, I have to constantly remind myself that I.am.ONE.person! I travel with two dogs and a cat. I so do not need a camp kitchen that can feed a dozen people!
So my camping cast iron collection is limited to a frying pan, a grill grate, a mini-hibachi, and 3 dutch ovens: 6qt, which mostly stays home, 3 qt - the perfect size, and 1 qt which is too small even for one and is more of a novelty that stays at home. Instead of a kitchen full of DOs, I bring
pie irons - perfect for one person.
I have a double and a single square cast iron Rome pie iron, and two antique round steel pie irons. When separated, they are great mini-frypans. Used as a traditional pie iron, I've made everything from homemade pot pie (for one) to grilled veggies to breakfast burritos to hamburgers. They're very versatile, relatively light and strong, and very portable. Really cuts down on the cooking equipment I need. And I plan my menus to take advantage of small amounts and cooking for one. I use a small 28qt marine cooler that neatly holds a block of ice in one half and the food I need for 3-5 days in the other half. I repack into smaller containers and really try to stick to my planned menu - which I cook from scratch as much as possible. My concession to camping is that I do use small (4-6) rolls of biscuit or crescent roll dough for pot pies in the pie irons, and frozen low carb tortillas for breakfast burritos.
I tried out a few different kinds of camp canopies. I ended up with the
TailGator, which attaches to either my rig or my Jeep Patriot with a gigantic magnet and bungee cords. Sly and Terry from Ontario had them on their tear last year at the TearUp in the Adirondacks, and I liked it so much I bought one. It's easy-peasy to set up. My other shade while camping is a plain old tilting patio umbrella with a weighted umbrella base. Opens or folds up in a minute, and provides just enough shade or shelter without too much cost in setup time or weight.
I think the easiest thing for me to make my time in my tiny travel trailer enjoyable was keep things small and simple. The less stuff I haul, the less work I have to do and the more time I have to just enjoy camp.
Hope that helps!