Somehow I just posted an empty reply. Meant to agree with Hoiho - it's really a matter of careful alignment. I don't think you can easily hold things in place without some physical aids - shims or whatever, but with patience it will slide in.
I can fit the nitrile gloves in my road kit, just not sure what to take in terms of other tools. Getting the wheel out is one thing, breaking and re-setting the bead another, and of course getting the wheel back in, hopefully without any damage to anything.
I've replaced a few tubes on the road and it's always a PITA, especially if you're trying not scrape things up: your hands, the rim, whatever. In the woods it's a little easier 'cause no one worries to much about scratching up a trail bike rim. Usually the bead will break pretty easily, as it goes flat it wants to roll off the rim anyway, and the tire is usually good and soft by then, but some of them can be a bitch. I've seen guys tilt the bike on the center stand, sneak the tire under it, then use the weight of the bike and the center stand leg to break the bead but that always seemed a bit risky.
If I were out touring I'd find some place to carry a vice grip style welding clamp, they work well at breaking the bead, but blowing the thing back up is going to tricky unless you have some type of compressor with you. I once pumped up a BMW tire with the bikes hand pump, then gently rode to the nearest gas station to seat the bead, but these days even that's a long shot.
I don't normally recommend converting to tubeless tires, and I'm not planning it on my bike, but if you don't feel comfortable doing tire work, especially on the side of the road, it does make sense.