I hear there are setups that you can get out there to fill your own tires. If you do, fill it so that the whole rim inside the tire is just covered. This way you have enough squish in the tire for when you run over a rock or hit a rut and the rim is not exposed to the air in the tire. Oh, and if you have the dealer fill your tires for you when you buy a brand new tractor, the $ should be about $0.60/gal. This, I think, is an at cost price, and they only do it with new purchases.
Attachment 296589
Edit: Price Correction - I meant to say the at cost price should be about $1.60/gal. My dealer said he put about 50 gal in per tire and that both tires would cost me $150. My tires are 420/70-24.