I would use the wheels of a steamroller, rolled on the circle off of which you fly. Then cut the grass short, and voila!
Seriously, What Ruslan and Randy say. I prefer going with larger, narrower wheels, too, even if it looks a bit odd. You shouldn't need to do anything with the tailwheel.
And don't fly on the field that Randy flys on -- it has had a taste for stunt landing gear, and once a field has eaten a wheel, it'll never go back to just eating the occasional coin or car key.