Welcome to Tractor Forum taylor07! You have definitely found a gem in the rough. A 244 with 4WD is pretty rare. These tractors in were the precursers to the current day CUT. They were manufactured from 1982 to 1984. Came with a 21 hp diesel engine (3 cylinder I believe)
That 4WD drive shaft will be costly. Probably in the range of $250 to $350 IF you can find a dealer who can get the part new and maybe 2/3 the price used. You may be able to have the old shaft straightened if you can't find a new or used one.
New tires will also be costly. Expect something in the range of the better part of $750.
The hydraulic lift can be troubleshot and hopefully repaired or rebuilt.
The seat you can get recovered or find a replacement at TSC.
The battery $50 or less.
Unfortunately these tractors sell in the $3500 price range in good shape. With scrap metal prices so high they are worth near 50 a pound for the steel.
You might try offering the guy $750; expect him to balk. He may give you a counter offer if you offer $1,000.
Before I did anything, I would make the guy start the engine for you on the spot COLD. (NOT after he has warmed it up before you get there) If the engine is in good shape, the tractor may well be worth $1,000 provided the other problems can be fixed on the cheap. If the guy uses ether to start the engine, I would pass or stand by your $500 offer or not come far off of it.
Anyhow, good luck on your price negotiation. The 244 is a cool little tractor that is handy for many small scale jobs. Plus the red and black looks good too! Let us know how you make out.