I've got a 1973 440b, they are pretty good little machines.
What I'd look at if it was me.
1. Are the center pins good?
2. How are the tires? Tires are going to cost about $1500 each, so that's another $6000 you could be spending.
3. How's the compression in the engine?
4. Is the hydraulic pump up to par? You can rig a pressure gauge to the blade cylinder. Should be a 1/2" O ring fitting. The pressure should read 2200 to 2300 psi, if it is below 1800 you will have to rebuild or replace the pump. John Deere wants $2500 for one.
5. Check for hydraulic leaks. Leaks in lines can be fixed easy enough, but if the steering valve is leaking that's another $1200 for a rebuilt one, if the blade valve is leaking.......well, they don't make those anymore and you'll have to upgrade. That's another $600. The transmission is the hydraulic tank on the 440's and it only holds about 5 gallons. It dosen't take much of a leak to leave you stranded, and if you're coming down a steep slope it can get pretty western.
6. Check to see if there is fluid in the front and rear diff's.
I haven't had to spend much at all on mine for the last several years, but I've spent 5 grand on it this year and it's going to need tires before the year's over. But it has paid for itself, and every dime I've ever put into it.
The 440 is the perfect skidder for what I do, and is pretty productive in small stuff. It is a lot lower geared than most bigger skidders, but it only has a 70 horse engine.
Oldtimer is right, it's a buyer's market in this economy. I'd try to beat him up a little on the price. You are looking at a 37 year old skidder after all.
Andy