Situation: During the last decade, I have accumulated significant losses from a rental property; the deductions I can get for that in every year are very limited, so there is pending carryover.
Issue: When I sell the property now, all those losses become deductible immediately; resulting in a large taxable income reduction.
Sounds good, but is not optimal - the deductibles are either higher than the annual gross income, or nearly as high; so by applying them in one year, I am 'wasting' a part of them.
I would rather apply only 1/3, and in the following two years the other 1/3's respectively (or something like that). This would result in low taxes for multiple years, instead of one, which adds up to more benefit because of tax progression.
Question: Is this possible directly? If not, is it possible through some creative (but legal) process?
One idea I had is to rollover a pre-calculated amount of 401(k) to 401(k) Roth in the same year; this would result in having to pay tax for that amount, removing part of the effect of the sale. That does not distribute the effect over multiple years, but at least gets me some future tax-free Roth money.
[I understand that I might need to see a CPA for this, to fine-tune it really. I am looking here for info about known and proven general approaches to the situation, in any]