USA Inherited IRA (Point of Taxation)

Dec 30, 2016
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United States
I'm interested in finding out of about the treatment of funds withdrawn from an inherited IRA. I understand that withdrawals are treated as ordinary income, not penalized but it's all taxed at 38%+ and I've been trying to spread it out $50k or so a year over 4 or 5 years. This will be the second withdrawal. I used the first to pay off all debt.

Recently I've become interested in investing in real estate, specifically flipping. Were I to find a deal that I'd like to use much of the remaining money on (~$150K), is the taxable portion calculated at the time of withdrawal or if I were to invest it and lose money on the flip (exiting before the close of 2017), would I be able to offset the IRA withdrawal income with the loss? Obviously I don't intend to lose money, but it's important to be able to fully weigh the risks.

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