Great post! I've been curious about the impact that trading / investing in crypto currency will have on my already nightmarish tax reporting burden. And I don't even make six figures a year yet (close but not quite).
I'm sure the government will make it as difficult to comply and report as they possibly can. Furthermore I suspect I'll have to refile next year when I inevitably make some trivial mistake and they make me redo it all over $50 or less deviation from what they think I owe them. This has happened year after year. 2016 I got it all right but the previous few years they kicked the return back and ironically all but once they ended up owing me more than I calculated. So they screwed themselves by hassling me which is nice but it sucks having to waste my precious time.
Eventually my goal is to leave this police state (the United States) and find a country that is decent to live in which won't make my tax reporting burden an outrageous and inefficient nightmare. In the meantime i guess all I can do is report it as best I can and hope they don't audit me over some petty BS. like I said, I don't make enough money for it to be economical for them to even scour my return and make me refile as they lose money doing it. But they don't see it that way. If they can spend $500 paying some bureaucrat to pick through my return with a fine toothed comb to maybe gain $50 they will. And they have before. Needless to say I hate our government and the IRS. The founders never meant for the fed govt to be such a monstrosity that literally ruins people's lives on a daily basis. End rant.
I look forward to discussing this at some point with you Sean. You have a lot of good insight into things like this.