Here is my situation. I am early-retired bachelor living a low-cost existence, generating taxable income via Roth conversions to take advantage of the 0% federal tax rate, and thus am enrolled in the ACA Medicaid expansion. And although I have tried to do all my investing within my IRA, I ended up making an investment in a non-IRA that might be quite lucrative, such that as a long-term capital gain, I would use up the 0% long-term capital gain bracket. However this income level is at about $40K, which is obviously much higher than the cutoff for Medicaid.
So I'm thinking about doing this: At the beginning of the year, when I will want to get out of a certain amount of position in this investment, I will sell up to a point at which I exhaust all my carried over capital loss and get me just shy of the Medicaid cutoff (i.e., if I had no other income events for that year, my income would be at that just-shy level), and then sell the rest right at the end of the year. As it would be the end of the year, it would have no bearing on my Medicaid eligibility for that year (i.e., I would have a window of a week or so to inform the Exchange about my new income, but the year would run out before then), and it would not have any bearing on the eligibility for the next year, since the income events of the previous year would not be expected to continue into that next year. I would think that I should be able to prove that the income events of that year were exceptional events that should not be expected to be repeated; at the very least, I would be able to do my taxes on Jan 2 and be able to give incontrovertible documentation of having low income again.
So what do you all think? (BTW, when I had facial hair, it was mostly of the Amish style, so I am Mr. Money Bearder.)