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the issue you run into is that things like Steam Calculator will give you the total based on current prices while depending on when you baught it can make a major impact. if you only ever baught say AAA titles at day of release (without discount) then you could say $60 bucks each, and be done, but if there are indie titles, bundles, steam sales, or just price reductions in there then everything goes out the window. then we haven't even started to talk about buying things from GreenManGaming, or HumbleBundle which each try to sell at a discount,
I know that I have spent a few THOUSAND dollars on steam, and Humble Bundle combined meaning that besides my saved reciepts from Steam, and HumbleBundle I could only value my entire library somewhere between 3, and 5 thousand. when I am pretty sure it is a fraction of that spent.
As said, it's a rough estimate.
EDIT...to answer this exactly is what I meant...sorry
according to IRS for tax purposes you are supposed to hold onto your reciepts for 7 years (in accordence with laws pertaining to audits), but technically you only need to do this if you are itemizing, and deducting things like sales tax, or file business taxes (Like Valve does)
I can see I bought COD:MW for an eye popping $40 back in 2008
If i wanted to i could add upp the email reciepts for every humble bundle or and other Steam keys i have bought over the internet but it's to much work. That calculated number is a good enough barometer for me.