OK, I'm exaggerating slightly when I say "Finally!". I've only used a Keglove once, but it was such a huge PITA to put over a 5 gallon corny, it feels like finally.
The solution to getting the Keglove and the internal ice-pack sleeve onto a keg more easily is to first put it on another cylinder of similar diameter. It's SO much easier to manipulate than a full keg. Once it's on that cylinder, and the internal sleeve is all tucked in where it's supposed to be, it's easy to then slide it off onto the keg itself. There are a couple of advantages to this besides the reduced swearing. One, you're not working with a 45+ lb keg and jostling the beer inside. Two, you're not warming up the keg and ice sleeve while you try to get it on there.
The question however, is what do you use for that cylinder? It's gotta be both wide enough and strong enough to handle the "pressure" the Keglove will put on it, especially when your arms will be alongside it moving the ice sleeve into place.
The answer is simple, and possibly free. A typical corny keg is about 8.5" in diameter. A piece of 8" PVC pipe is 8.625" in diameter (8" ID, 8⅝" OD). It's wide enough and plenty strong enough, and very easy to work with while you get the Keglove on it. The pay option is to buy a piece online, but expect to pay $40+ for a short section when you include shipping. I found an 8" endcap for $33 shipped, but it would have only been about 5" long, probably not enough to do much good.
The possibly free solution is to call around to local plumbing supply businesses or industrial plumbing installers and see if they have any scrap sections that they'd be willing to sell. PVC that size is rarely used in a residential setting, so you're not likely to find it in a big box store. I live in a fairly small town, but both places I called said they could help me. One said they'd have some in about a week when they finished a job, but the other had a 5' piece sitting there, so I went over and sawed off a 15" section at lunch one day (not an easy task, BTW). It's long enough, but if you have the option, get one closer to 18". The top 3"-4" of my Keglove are not on the cylinder, but that's not a problem since I'm starting on the other end anyway. Make sure you draw a line around the PVC before cutting it.
They might charge you for it, but it should be much cheaper than buying online. The guy who helped me said it would be about $5, but after telling them what it it was for, they gave it to me for free. I returned about a week later with a couple of bottles of homebrew (I hadn't tapped a new batch yet when I got it).
When you get the PVC home, you'll want to clean it up a bit. Besides physically washing it, I rounded off the edges with a file so nothing would snag on the neoprene. I also took a piece of fine sandpaper and smoothed out any nicks and cuts along the outside, again to avoid snags. You'll still have gouges, but they won't be rough. My Keglove is in my freezer wrapped around the PVC, ready to be dropped over my cold keg for a beer fest next weekend (no pics, don't know how to post them).