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If everything goes to plan, this year I will become US resident. Either because I get my green card before June 1st or under the substantial presence test on that date.
My first question was my tax liability date. After reading a lot, I came to the conclusion that if I get my green card, then it will be the day it is approved, I will then have the choice of pulling it back to January 1st, be able to claim standard deduction, but pay taxes on my worldwide income for the whole year. But under the substantial presence test, it will be my first day in the US which is January 1st. So anyway I will have to pay taxes as resident this year. (Until now I pay as NRA with 1040-NR).

Now the remaining question is what is the cost basis and holding period for my stock and options.
As a foreigner I was not subject to the wash-sale rule, so I never accounted for it. I have been trading options for some 15 years, mostly selling weekly CALLs and PUTs and rolling them week after week.

Do I have to redo all my accounting for the last years to apply the wash-sale rule retroactively?

I understand that stock pays gains based on the original purchase date even if it is before my residency date. Is it the same for losses?
What about options?
What about straddles, diagonals, SYNs, BCSs?
Can I put my transaction logs for the last few years in a software and get the cost basis for my current portfolio?

Thanks,
Juan
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