Driving it up should work fine. It *may* not be enough on my stupidly-tall trailer to still be able to open the door because of the cables that "help" raise and lower the rear door/ramp, but it should be fine on most. I didn't think about doing that, but then again I never gave regular
As for what to pull with, I thought pretty much all new cars had a small pop out piece of plastic bumper and behind it was a screw attachment point for an eye-bolt (that should be with the tire changing stuff). That way should you need to get put on a rollback there's a "safe" place to pull from. It shouldn't be a big deal to screw that in and out, though on some cars (notably my Porsche Cayman), the plastic piece doesn't appear to be made for repeated use.
Oh, I don't have the toter any more. Just sold it. I now have a Freightliner Sportchassis with a single car gooseneck trailer that has a small bathroom in it, and have a used motorcoach on the way with a new two car stacker to go behind that. It's a 26' tag, but it's like 13' feet tall.
Can't think of any real outfitting do's and don'ts. Just be careful when putting screws through the walls from the inside so they don't poke through the outside.

Assuming you don't have AC on the trailer or anything, get a small generator and a fan/blower to take with you. Enclosed trailers make a nice place to get out of the sun, but even with all doors open the solar gain can be a bitch if there's no moving air (such that going out in the sun can be a better choice!). If you have 12v lights in your trailer I'd highly suggest getting one of the solar panel trickle chargers to keep the battery in your trailer topped off. That will extend the life of your battery since it *would* otherwise die from sitting over the winter at the very least. Plus it can save your butt if you leave the lights on.
One thing I added on my prevoius trailer was an 8 gallon water tank from tractor supply. Also got a pressure regulated water pump (like RVs use, except I got one from TSC that's for garden sprayers...same pump, but a lot cheaper). I put it on the tongue because I needed tongue weight on that particular trailer and plumbed it to a spigot on the outside. Then you've got a nice way to wash hands at events. I don't mind using port-a-potties so much, but I do hate not being able to actually *wash* my hands. Anyway, you could put something like that inside easily enough. Heck, mount it up on the wall (obviously would need to be fairly sturdy as you're talking about 60+ pounds of water) and skip the pump and just fill it at home with your garden hose. Take a hose with you and you should have enough pressure outside to wash hands easily enough.
There are lots of great gadgets made by Pit-Pal for trailers. Some worth it, some maybe not. I'm not a great fan of their chair rack. I do like their strap rack. I like "L" track much better than "E" track, though in a plywood wall/floor trailer the E may be smarter (you can use more screws to anchor and just anchor to wood...with L I'd make sure you were going into some metal).
Your car may have T-hook holes in it. If so, get some T hooks and use those to tie the car down. Not sure where to get them, though...my set came from Bob Tunnell via GH Sharp, but I don't know if that's because Bob sells them or what (only my Cayman uses them).
Always throw a strap in your wheels to strap them to your rack if you get a wall mount rack. I do like those, but tires can come out of them. They usually can't bounce out as much as they can turn on their sides and vibrate out.
There are lots of places you can buy pre-made cabinets or even custom ones for trailers. I like having some cabinet space. The more the better, in fact. Exterior lights are overrated. Hardly ever use mine. Beware of items on the floor vibrating around and rubbing up against the car (though plywood floor trailers are really good about *not* letting that happen generally).
Use only Tekonsha brand brake controllers. Period. Use LED lamps wherever possible. Trailers are notorious for killing fuses on tow vehicles for no apparent reason. This is far less likely if you reduce the current they can draw.
Okay, maybe I do know a few dos and don'ts. Probably not much that isn't pretty obvious, though.
--Donnie