ikandiggit, this is a great question for ones newer to the hobby. First, do you ever see the condition listed alone with the auction on most of these? The Scott catalog is still just a guide not a set in stone price. Also, the prices in Scott reflect a very fine condition price when most of these auction prices are selling at 20% of Scott reflecting a lower grade stamp of average or good condition. This difference in grades can make a large price difference. Take also into effect gum condition on older classics or amount or type of cancel on some and prices can vary greatly.
In conclusion, much more time must be spent to know just what should be paid on certain stamps or the type and condition. Time, knowledge, research, and what you are already doing as to watching auctions will help train you to get a better feel for what is it really worth.
Of course if you just have to have it some, the sky is the limit.
