Hmmm...that is going to be quite a bit of work. Trust me, I know.
The cup is ALWAYS yellow, so that has to be replaced if you want it nice, but it's only $50. The ramps are easy to clean with Novus 3-2-1 and a brief flame polish (if you've never flame polished though, be ULTRA careful. PM for details on how to do this. 1 second too long and the ramp is ruined). The adjust failure is most likely just a dead battery. I just bought my 2nd Diner with an Adjust Failure. New batteries took care of that. Check to see if there's any alkaline leakage though as that also could cause that error.
IF you can wait till CPR comes out with their playfield (and seriously, who knows how long that will take. Usually what they report on their site is not as accurate as the rest of us would like), then it might be a fun project. You'll have an excellent playfield (and their stuff is quite good), an excellent cab, and freshly cleaned ramps/cup/etc... I don't think you're getting a "deal" by any means though. After all is said and done, you're looking at around $2700-$3000 and probably 30-40 hours of work for that Diner. Granted, it will have a brand, new playfield, but you've got to decide what you can afford to spend.
Personally, if I had the space to store it and patience to wait, I'd be tempted to pick it up. I'd probably end up passing though unless he went down to $1k due to lack of space and a wife who thinks rationally about investments (a dead Diner w/no inserts would be a hard sell).
I also LOVE working on pins. Diner is not an easy foray into pin restoration due to the back cup assembly. It's a pretty beast of a tear-down. I'm more than happy to help you with pics and tips if you decide to go this route though! It's definitely a fun undertaking, and is a great way to spend some summer nights in the garage.
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I'm going to be selling the Diner I just picked up (the 2nd one) in about a week or two. Here are the details:
PF is a 7.5/10: really nice but has some mylar bubbling in typical places on this game and minor insert lift. Cab is a 6/10: no wood showing anywhere and shaped fine, has scratches/slight fade from being on route, been touched up with black where needed. Backglass is a 9/10, as is the display. No errors and plays fantastic.
Game will:
1. have brand new legs,
2. have brand new speech and music chips,
3. have new balls,
4. be completely torn down and cleaned with Novus (then, it will be fully waxed),
5. re-rubbered with new rubbers,
6. ramps will be cleaned with Novus 3-2-1 and flame polished to look fantastic,
7. every bulb checked and replaced where necessary,
8. metal guides and ball trays will be shined up via steel wool,
9. inside of cab will be cleaned out,
10. have several other new misc parts where needed.
Not sure what my asking price will be yet, as I'm waiting to see how it all turns out. PM me if interested.