If you're tires are like mine were, you're gonna need luck
I know it will help if you get the wheel/tire good and warm w/ that hard,old rubber tire to make the rubber a bit more pliable to flex enough to get it over the rim.
Amazingly....
I did it! First time successfully using a tire iron - sweet! Thanks for the recommendation grcamna, this style iron is definitely the easiest to use. I used the large black handle to do a majority of the pulling, and the small silver ones to push the bead into a position where I could grab it, or to hold a bead I'd already lifted.
My strategy as follows. I first took the 16" iron, got a good hold on the bead using the hook and the curved head, then lifted it above the rim. I then replaced the large iron with one of the smaller irons to hold the bead in place. Next, back with the 16" iron, I would move about 3" away from where I now had the smaller bead holder. In order to grab the bead in this new location, I would have to lower my previous "grab" partially. So, with both irons in hand, I'd rock one down just below the rim - enough to relieve pressure for the longer iron to grab, but not so much that I lost hold. Then I would raise both above the rim at the same time et voila - 3" of bead above the rim. I would again replace the large iron with a smaller silver one, move 3" down, and attempt to repeat the same process. It's not as easy as the above is maybe making it sound, but with some finagling it is definitely doable.
Now I have this...
I was inspecting my rear sprocket and came to the conclusion that it looked relatively worn. Maybe a new one is in order? I thought the distinct angling of the teeth in one direction was a sign of wear. Somebody please correct me if I'm wrong.
Thanks!