I'm going to open an offshore account and was wondering if there is a relatively easy way to ensure compliance with the IRS. Offshore brokerages don't offer 1099-B's and I'm not aware of anything like GainsKeeper that works with offshore brokerages. Any ideas?
You've got way bigger issues than 1099s like FBAR and depending on your assets the other FACTFA filings like the 8938. Plan on hiring someone to do this for you, and then ask yourself if it's worth your while in the first place.
Tick the box that acknowledges an offshore account on the 1040 and report the activity. It is a ton of work and reporting so as others have said -"why"?