About the blind-folding... I don't know how he new to step up, but he did. His legs were wrapped and I think he bumped his front legs on it and figured it out. My friend was also telling him "up." Most horses are calm when blindfolded, they can't see and most have the sense to not move. But if you just go up to a random horse you've never met and blindfold him without having built the trust it wouldn't work as well. =]
You could put a tie down on if you had a surcingle. However, you may not want a bunch of stuff on him when you're trying to load, and you also don't want him to get "stuck."
I think it was good that you had to go to school. One of the most important parts about training is stopping on a good note. So many people think, "Oh, that was great, let's do it again!" and both you and your horse will get frustrated when it's not as great the next go-around. If you have a chance to load him in the morning and again in the evening that's fine, but I wouldn't do it right in a row so you don't get in an even bigger fight.
While I don't believe in with-holding food or water, you could put the horse trailer in his pasture, attached to a vehicle so there's no way for the trailer to move, and feed him his grain and hay just inside the trailer. You would have to ALWAYS feed him like that though, that way he can associate the trailer as his source of food. And just gradually put it farther back. You said he will walk in on his own anyway, but now we're just making the trailer a really good thing, because it feeds him.
Huh. I guess it just seems a little weird, since I've never really heard of that being done.
Yeah, I was more or less joking about tying his head down. It just always seems like he hits his head, and then it gets that much harder to load him the next time. My dad says we should find him a helmet, so he won't kill anymore brain cells.
That actually makes a lot of sense... more so than my uncle's "get the horse in at all costs, take him out, and do it all over again until the horse just loads without a fight" -- I'm usually a little more patient, and consider it a small victory if all I can get is the front feet in a few times, but I've still always gone back and done it again.
And for feeding him in the trailer... we usually keep a trailer in the pasture year-round -- it's their shelter, really, not counting the forest. We used to keep their mineral blocks or hay up front for them, too, but they'd get inside and get to fighting or something, so I try not to feed them in closed spaces anymore. And we don't really have a way to keep him in his own little pasture for anything longer than a week.