Unless they're lucite, the stems will probably be green/oxidised. So you can expect that. What you look for is deep tooth marks from clenching. The fewer (and shallower) these are, the better. Is the button nearly gnawed-away ?
The next thing you check is the top and rims. Did the guy beat the dottle out of them against an ashtray or a wall, leaving them all scarred ? Will this bother you if he did ? (If you really like the pipe otherwise, it probably will).
Even more important is the inside rim. Is it all charred out of round from careless lighting ? (That can be hard -- even impossible -- to judge if the top's all crusted over with solidified tar).
Check the bowl walls for dark spots that can (but don't necessarily) indicate an incipient burn-out from smoking too hot for too long.
Try running a pipe cleaner through each stem. Can you reach the interior of the bowl with it ? (Snip the end of the cleaner off cleanly with a wire snipper first so you don't have a hook edge that can catch on the way through and give you a false reading). If you can, that's a good sign. If not, twist the stem out and see if the drilling's concentric with the mortise or not. (Bent bulldogs and similar pipes will almost never pass this test but can still be good smokers)
Then again, the airway might be just crusted nearly shut from not having been well-enough maintained). If so, and you get that pipe, use drill bits (hand held in a tap wrench and very gently going from smaller sizes up to bore diameter) to shave the tar away. Forget alcohol on cleaners entirely.
Try drawing air (or blowing) through the stems. (This will obviously be related to whether the airway's crusted up or not). A free draw is a good thing. A tight draw you have to guess a little about.
Finally, do you just flat-out like the pipe ? If you do, you'll probably spend more time getting it right once you get it home (and getting right with it) than if it's just something to smoke.
Another factor is, who made each pipe ? "Name" pipes (Stanwell, to pull one out of the air) are better bets than a "Genuine Imported Briar." But then again, many of these were made by "name" companies. In the final analysis, you're getting a pipe. Not a name.
Finally, does it smell bad (either sour or ghosted with yucky shampoo/candy stuff that's going to color every bowl you smoke in it for years to come) ? If so, you're looking at sending it to Dr. Dave to be Ozoned, at least. Possibly re-stemmed, re-finished, &c. to put it back to 100% again. Factor this cost (Ozone $5 + mailing each way) into the equation.
Estate pipes can be craps-shoots even when they're cleaned up ; raw ones increase the guessing factor, but generally sell way cheaper. So don't get bummed if one doesn't end up working out. In the long run, the better you get at evaluating raw estates and doing basic clean-up, the more you'll be able to stock your racks with better pipes at lower cost than your bros here who need their hands held (reputable sellers with good feedback on Flea Bay, multiple sharp pictures, return policy, &c).
Rome wasn't built in a day.
Happy hunting !
:face: