The others are right, this is hard on the tractor, in particular the regulator and battery.
That said I've done it, alot...
DON'T leave the cables on for a long time, and DON'T use cheap cables. Mine are a real good big set that I, uh, swiped from a well drilling outfit. They used it to jump 24v systems, its hefty. My great Uncle had a cheap set any finally the connections where the clamp and cable meet wore out.
Oh, like the others said DON'T let the truck touch the tractor!
You might as well plan on a new battery though, theres going to become a point where you'll get tire