Great stuff...I have two sides of the street....as a preparer and a filer...
This year is more nerve wracking than headache as I was shocked how many crypto trades I had done....90% coin to coin....I don't like having such a big number showing on my tax return as audit chances increase...and the net gain was enough to cause considerable pain writing checks for amounts I barely had in value due to coin market crash...
I also lose some sleep on the foreign account filing as it puts me in the league of some tax avoidance criminal with secret overseas accounts even though its a bunch of digital coins located who knows where for sure....
As a preparer....I've had the nightmares of not e filing client taxes only to find out later and have to eat penalties....or e filing a "return" instead of an extension before the numbers are even in the system....or suddenly have a client show up with some notice from a foreign bank I knew nothing about....and while its never pleasant to have a business client show up with an audit notice....its a lot more of a nightmare when IRS criminal investigators show up at my office concerning a client's irregularities....
No wonder I have gray hair and stomach issues!
Well....time to pop one more Zantac and go back to my tax program as I try and finish up a few more last minute client returns by one more final tax deadline...happy 2017 tax season end on October 15.
Sounds like we've shared many of the same fears.
I've actually never held crypto directly for myself, only via the company. When we first got into crypto, the regulations just weren't clear enough that I was certain how the US was going to handle it, so whenever someone paid me in crypto for work, I immediately converted it to cash. When we decided to start trading it, we opted to start up a company overseas and confine our crypto trading to that company as it didn't have all the ambiguous rules that the US was suffering from at that point in time.
It was a lot of work to setup an overseas company and at the time it was a big expense too, but I've never regretted it for a minute (despite the increased tax complexity that I didn't realize at the time I was setting myself up for).
But even with a foreign company, you can't escape the FBAR filings, and having to file those things gives me the same fears that it might trigger an audit. Oh, and the fear that I'll forget some minor foreign exchange I opened an account on and only did one or two small trades on and be hit with a huge penalty for some small amount of money. The FBAR filing rules are crazy, IMO.
Hang in there, the worst is almost over (well, as long as you don't have any audits afterwards)!