Wow good read. I think at the end of the day....Talk to a CPA of a financial professional professional. We can talk about it and go back and forth but what ultimately matters is what a CPA thinks. If Jerry is smart and really making a significant amount of money he is going to hire 2-3 accountants, and a few lawyers.
Never rely on one persons opinion-get two or three opinions.

Lastly, the correlation point of WoW Gold and Counter Strike Skins is a stretch BECAUSE it is not an INCOME producing Asset. It does not generate revenue for the user. Revenue generating is a TOP focus for the IRS. Because if ANYTHING its making money they want to know that you are making money.

I am not a CPA or a financial adviser. I am sharing my personal story.
Thanks