I have never really found it all that difficult to get the tires on the wheels. i just lay my wheel up-side down with the axle hole facing up, and press the tires over the wheel. It seems to be pretty easy that way.
Now getting the axle in the back of the wheel is a whole nuther story, and this can often be pretty difficult. I usually take the wheel (with tires already on) and place it up-side down again, then take the axle and hold it on the hole, take a pair of pliers (using as a small hammer cuz i dont have a small hammer lol) and gently tap the axle into the back of the wheel. You have to try and make sure the axle goes into the back of the wheel as close to straight as you can, which I dont always get right on my first attempt. I can usually straighten the axle out to be pretty close to straight by just gently bending it while its still in the wheel.... Then I take the axle and wheel and slide it through the axle holes on the equipment, take the other wheel (with tires added) and hold it over the axle so the wheel hole is on the axle, take my pliers again and tap the wheel till it is on the axle. Its often hard to get it straight as well.... But again, I can usually get it pretty straight by gently bending the wheel on the axle. I also have to push the tires on each wheel back out so they meet the rim of the wheel after the axle has been installed....
You can also drill the axle hole on the wheel out slightly with a bit that will just barely not fit in the hole (im not sure what size drill bit it is lol). I usually dont do this however because most of the time that results in having to glue the axle into the wheels to keep them on. This is okay if the equipment is finished and will not have to be taken apart again though....