If you could get one or two reasonably priced comics signed by Stan Lee what would you have signed.

Frankly, the old ones are probably the best to get signed and those tend to be pricey.

However, a cheaper classic is the Secret Wars series. The trouble is finding them…

Otherwise, any Marvel comic that he likes is perfectly fine.

The cheapest one I can think of that would still be cool would be to pick up a hardbound Marvel Encyclopedia. I think they run 20–25 bucks. I can’t think of anything cool that would be that cheap.

Depends on how much your friend is willing to spend. While I agree with @King_Pariah that the coolest (and ultimately most valuable) would be a really old comic, the best thing would probably be to buy a hardbound anthology and have him sign that. Hardback books last a wee bit longer than other types of printed materials.

Have him buy two of the hardbound books (Iron man!), then he can sell one afterwards.
He will have doubled his money (at least) and still have one.

My Essential Iron Man trade paperback, just because it’s delightfully old skool.