I don't think it has to be such a headache as long as you keep records. What I plan on doing is calculating my gains and losses using https://bitcoin.tax/ and bringing the report to a CPA to check over.

Not sure about the "paid immediately" part. That's news to me actually. Can anybody else weigh in on this?

Edit: https://www.irs.gov/faqs/estimated-tax suggests you do if you expect to owe more than $1,000 in taxes.