I'm one of the club fixit guys, and I got a little obsessed with the task of mounting a tire on a Tost 3" dia. solid tailwheel. I tried all the good advice offered on this and other forums with zero success. Most likely I lack superhuman hand strength and three extra arms.
Success took the form of a $43 Harbor Freight mini-tire changer and Ru-Glyde tire mounting lubricant from NAPA Auto. It's not as easy as the harbor freight promotional video:
https://www.youtube.com/watch?v=v7o-i4tQyfY
but it isn't a hideous trial either. With the tool the most difficult part is getting the inner tube emplaced and managing the valve stem.
Brian R
127MM
PS, If you used the tool regularly you'd probably make some modifications, since it theoretically is for wheels 4" dia. and greater.
PPS, I bought a split wheel for my own glider. Expensive, but you have some recourse if you get a flat when away from the shop.