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Taking along one or more folks that have experience with Model A's is one of the best things that you can do. I've helped several people interested in purchasing A's by inspecting the cars for them.
I take a bright flashlight with me and spend a considerable amount of time crawling around and under looking things over.
One of the things that I have found that gives a quick idea as to weather or not a car has been maintained/set up correctly is the position of the brake levers. If you see all 4 of them set to the proper 15 degrees forward it is a good sign.
I'll take along a jack, jack stand and three jaw puller so I can take a look at the brakes and bearings. (Bring cotter keys with to replace the ones you remove)
Of course a compression test will give an idea as to what is going on internally with the engine. Hopefully they have documentation on any engine work. If the engine does not run I tend to err on the side of thinking that the engine probably needs significant work/repair.
If the car has potential I can easily spend 3 or 4 or more hours looking one over.