Either is hard on the inside of tires. Can you use it occasionally, yes. Another way is to jack the skid steer up, allowing the tire to hang in the air without touching anything. Wrap a rope around the center of the tire and tie it, then twist a bar in it to start shortening the rope. A small ratchet strap will also work. Tightening around the tire tread in the middle of the tire forces the beads outward, so that you can add air. Be sure and remove the guts from inside the valve stem so that you get the maximum flow of air to seat the beads.
Might want to put the skid steer up on blocks when not in use, or just get in the habit of adding a little air once a week or so.
David from jax