Can't believe nobody has responded to your thread yet. So, I'll give it a shot. The main item is always to check for rust and rusted out body panels that have been replaced or repaired. Floors, trunks, rear quarters, and rear frame rails are parts that usually show rust damage first.
If the owner is asking a high price, claiming a numbers matching car, then you should check all the numbers you can, to see how many actually match. If it's not a matching numbers car, check out the engine. You typed "...400??????". So, if it's an original 400 car it will obviously have a 400 hood, with the twin scoops. And I think they had a Pontiac arrowhead in the center of the front bumper. But 400 stuff can be bolted on. You'll have to get the VIN # and the info off the cowl tag and possibly get a PHS report on it to find out exactly how the car was equipped from the factory.
Whether or not it is a real 400 Bird, it can have all sorts of exterior, interior and mechanical parts that were not original factory items, such as the entire drive train and cooling system. A couple of the real popular items are the Camaro front and rear deck spoilers. Aftermarket steering wheels are popular, as are aftermarket seats, shifters, and wheels.
Saying a motor was rebuilt, means absolutely nothing. Rebuilt means different things to different people. It may have been done by someone who knew very little about a Pontiac engine. The very cheapest parts available may have been used, such as the 8-eyebrow pistons and the stock cast rods. Or, it may have the original pistons with fresh rings and bearings. And since most Pontiac V8's look very similar from the outside, you must check the block casting number and head numbers, to even know what block and heads is has, much less what parts are inside. When buying, I would always assume that the engine will probably need rebuilding or replacing immediately or at least very soon.
MOST sellers always ask more for a car than it's worth, and more than they really expect to get. So, if they really wanna sell it, they will always take less than the asking price. Most of the time it's sorta like buying a used house. The buyer has an asking price. You go thru a realtor and make a lower counter offer. Then the seller comes back with a slightly lower price, but higher than your offer. Then it continues this way until a price, somewhere in the middle is agreed upon, or there is a no sale.
I have run across a VERY FEW guys who set a firm price and would not budge off of it. Most of the time, but not always, the car is not worth quite as much as the asking price. Many times guys really don't wanna sell the car, but will sell, if they can find somebody willing to pay their high price. And if they have a nice car, there are usually a few people around with plenty of spare $ to buy the car and really don't care if it's overpriced or not. Hey, this is just the way things are. There are not many bargains today, on 1st gen Birds, because so many people know what they are worth. But if you can find a good clean car, for a reasonable price, you should be able to get pretty near what you pay, when you decide to sell.--NO GUARANTEES !