One thing is for sure- you will be stressed, if you're anything like me! That's okay though! Like my adopted grandfather (he's 75 and trailers his two Percheron mares all over and drives them in parades. He also had two QHs on the Wells Fargo wagon, so he knows his stuff! ;)) the horse will be fine once you get going.
For his legs, go for boots, not wraps! The wraps could come undone, and he could trip and fall out of the trailer... Not a fun experience. A light blanket; maybe a sheet? should be adequate. Just be careful he doesn't sweat. Sweat is your enemy with cold. A good nylon halter is what I've used, and I really haven't had issues.
Use a hay bag, not a net. If you have a trailer tie with a quick release end, use it. I love mine to death. Super handy when he gets a little excited about backing out. :)
As for the driving, I once heard an example such as- "You are hauling a trailer full of water, try not to spill a single drop." Nice and slow, wide turns, leave extra room for braking!