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i agree with the first reply. KBB and edmunds mean almost nothing with regards to 15 year old cars anymore. The market is totally in the buyers hands. I don't know where you live, but I'll give you my opinion for Maryland. I bought a '91 240 here 6 months ago, so the datapoint should still be relevant.
I looked at 240's for about 4 months, working on a car for my daughter who got her license last Friday. I wasn't in a hurry and I was willing to go out and look at several cars. I found most people have an over-rated opinion of the car they are trying to sell. As in your case, a car that is otherwise an "8" is actually a "5" at best because of the a/c and transmission problems. They are significant and would have been fixed, IMHO, by the seller before offering for sale if they involved a simple solution like a relay. That said, the car is still worth considering, just nowhere near where you're at in the discussion.
I found the car I eventually bought an hour away and here is the condition/price I found it in: 118k miles, good paint, good interior, well-maintained by Volvo experienced shop, crack in windshield, minor trim pieces missing; a/c, tranny, engine, etc.. all appeared to be working fine. It was state inspected in VA, but I live in MD so I'd need to pay for MD state inspection. Seller was asking $3900. I called him after the car was advertised for 4 weeks in the Washington Post. After 10 minutes discussion, I told him the car sounded ok, but I wasn't prepared to meet his price, thanks anyway. He came down over the phone to $3000.
When I got there and saw the cracked windshield and overall condition of the car, I got him down to $2700. I probably could have pushed harder, but I'm not into lowballing people to see how hard I can squeeze them. I had to replace the windshield, front brake rotors, and align the front end to pass MD inspection. All told, I paid another $350 getting the car on the road. It's a great car and I expect to get at least anohter 150 k miles out of it.
I hope this helps give you a sense of where you need to be when you're looking out there. I don't doubt there are $5000 240's out there, I just don't think I'd ever be the guy shelling out the $5000. You should be able to get a very good car for $3000 max unless you're in an area that worhips 240's.
good luck,
someguyfromMaryland
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