Take this with a grain of salt, as I collect classic-era foreign, primarily, but I wouldn't even think about investing in getting something graded unless it was mint, never hinged, sharp, bright, with no detectable faults, and centering that seems really, really nice as you keep turning the stamp 90 degrees at a time. (I find that looking at a stamp upside down helps me judge some things more fairly...may be silly, but it seems to work for me.)
Not necessarily.......listing things at Scott values will not attract bidders. Most stamps sell for about 1/4 - 1/3 Scott........unless you find something that is especially nice I would list most at .99 cents and see if they attract bids. The mint #319 strip looks nice at first glance but centering means a lot to many collectors and will more than likely keep bids lower than they might be if it were centered better.
As you are just beginning, I would suggest that you sort out the items you'd like to keep.....learning about them will help you make better decisions about how to go about selling the ones you don't care about. One thing that might help is to check out auctions of the material you'd might want to sell......it will give you a better idea of true market values.
Unless a stamp is in exceptional condition, and worth at least $100 I personaly wouldn't even consider getting it graded. Even then I would think twice.
You can expect most stamps on ebay to sell for 25-75% of Scott, with rare exception.
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