Things to check for... (you have your work cut out).. don't just assume it'll be OK cuz you're buying from an established dealer. Be meticulous. You're dropping your dimes on this so there's nothing wrong with being a little anal about the details.
1. Tyre Tread.. is it deep enough? Some cars are expensive when it comes to tyres.
2. Tyres .. all the same brand and same sizes? Are they the right size for the model?
3. Paintwork = Always check in the creases for any bubbling cuz that means rust.
4. Speaking of rust... check the underside of the car.. are the bits of the suspension in good order? Some modern cars are all covered up under there so you might want to take a mechanic friend with you. Either that or get a stranger and pay him $100 for his trouble. Better that than ordering a new suspension.
5. Interior electronics.. working well? Fans? Heaters? Seat adjustment? Sat-nav? How about headrest adjustment? Any warning lights?
6. Have a look under the bonnet... no funny mods? Good. If you aren't up to scratch, that $100 for the mechanic might be well worth it.
7. Exterior lighting.. check all beam settings. Check interior lights aswell.
8. Interior switches.. have a little tug and twist. Many 'non premium' cars have questionable build quality. Chances are, the switches may have fallen off at some point and the owner is just praying you don't touch it and find it that it falls off. Press and twist everything.. unless you don't mind dodgy switches.
9. Interior leather/cloth quality. Have a proper look. Look within the seats, under them e.t.c. Most cars have been puked on... people have got a little too excited in them and bodily fluids have been excreted. Not a big deal as a good professional clean will sort it.. but sometimes you'll find stains, cuts/tears/holes in the leather.. too much creasing (a sign of heavy use.. high mileage... check the leather if you think the mileage is too good to be true).
10. Service history - Critical. Full service history from the dealer or an expert independent garage? If it wasn't, I'd walk. When was it last serviced? This may not be a big deal but check the mileage between services. I can't give proper numbers because it differs with every car but a car serviced over a year ago.. be careful.
Also, a car that was serviced a long time ago and hasn't had much mileage on it till now.. be careful. Might be a problem car. then again it might be that the owner just didn't use it hence the sale. Your mechanic companion would help.
11. Mileage - I don't know about American cars all that much but in the UK, most cars are NOT chain driven. They have a cam belt (timing belt) which is a bitch to replace on most of these cars. Most of the time they say it's an engine out job and so it costs a lot of money.
I'm pretty sure cam belts should be replaced every 50,000 miles. If you potential car is hovering around that mileage, ask if the job's been done. If it hasn't, either budget for it in your negotiations (I'd say around $1000 off) or look at other cars. This is especially true for a performance car with a smaller engine.
High mileage MUST have a full service history. It's not really a reason to walk away from a car as some cars with 100,000 miles on them run better than those with half. It comes down to maintenance.
12. History - has it been in an accident? Stolen before? Bought in an auction after being impounded? Do an HPI check. You don't want to be driving a car that's been welded together by an amateur underneath after a big accident for obvious safety reasons.
13. Test drive - How's the ride? Crashy? If the rims are under 18" then that's something to be concerned about (suspension or tyres). It's all relative and it depends on the car. I'd test 3 different cars of the exact same model before making a decision. Test the handling too.. Most cars have a tracking issue... they tend to move to one side if the steering is in a neutral position. That could be a fucked up suspension or just a tracking issue. If it's a tracking issue, negotiate it into the price. Should be like $50.. don't know.
Rev the engine all the way to the red line and listen to how it sounds. Any weird clattering? Does the engine hesitate when you give it the beans? It should rev freely if it's a small engine (inline 4/boxer).. or smoothly and lazily if its a v6/v8. Basically, nothing weird should happen. Might help to have mechanic in with you.
If it's a manual, how's the clutch travel? Here's where comparing with 3 different cars of the same model helps. Also, is there too much judder when you lift the clutch to the bite? Do you sink your foot and the revs go up but your car doesn't go faster? That's a slippy clutch.
Gear shifts.. overly tough? Usually, if changing gears is too much work, something is wrong with that gearbox. It probably needs lubricating.. or its worn cuz the driver was shit at driving manual.
I have no experience with autos.
Styling - Look out for any scratches, grazes and ESPECIALLY fucked up wheels or Curbing/Kerbing. Factor the cost of restoration into the negotiation price.
Look inside for general wear and tear. Some people smoke in their car. Does it smell like smoke? Unless you smoke too, I'd leave it. I'd also check for cigarette butt damage.. it burns carpets, seats and dashes.
Always check for chips in the windscreen.. a given.
Finally... EXHAUST!!! This fucked me when I bought my car. Check to see if its mounted properly. Also, check for any cracks/holes in it. Check the entire exhaust man. Does the car sound funny? does it run clean? It's not overly smokey right? If it is, something ain't right....
There's probably more.. but after years of watching Wheeler Dealers, this is what I can remember!