Disclaimer: I am not a lawyer, accountant or investment advisor. I have not tried this, and I'm currently trying to think of reasons why it won't work.
How to Beat the Tax System:
Suppose one had an investment account and a Roth IRA. Suppose further the investment account had a realized gain for the year. From the investment account, one could sell-to-open a way out-of-the-money cash-secured put at a high limit that no one would buy. As long as you're the only open interest, you could then buy your option in your other account. You'd in essence be swapping short-term gains for tax-free savings.
You're hosed if another party rushed in to sell you the put at a lower price, but the savings could easily exceed the cost of commissions if the option is thinly traded enough. I suppose you could just take the market price on both sides, though, if you're willing to repeat the process until the transition goes the "correct" way.
You can withdraw penalty-free from the Roth IRA when you buy your first house. Or, you could simply reverse the process as needed. This could be particularly helpful if one were having a bad year and had lost more than the maximum investment-losses deduction.
Any downsides to this bit of financial munchkin-ism? Does this constitute tax evasion? I imagine it wouldn't be provable for anyone other than me (you're welcome). Are there actually options that thinly-traded?
I am not a tax lawyer, but I suspect the IRS would treat the put-option sale-thingie as a deposit into your Roth IRA ("substance over form" is a recognized tax law doctrine, at least when it benefits the IRS). Likewise, reversing the process likely would be classified as withdrawing from the IRA. So, the general rules for deposits and withdraws from the IRA would likely apply. If I understand your suggestion correctly, the general rules would prohibit most of what you are trying to do.
In short, I don't think your plan does what you think it doe...
Thus spake Eliezer:
It seems that many here might have outlandish ideas for ways of improving our lives. For instance, a recent post advocated installing really bright lights as a way to boost alertness and productivity. We should not adopt such hacks into our dogma until we're pretty sure they work; however, one way of knowing whether a crazy idea works is to try implementing it, and you may have more ideas than you're planning to implement.
So: please post all such lifehack ideas! Even if you haven't tried them, even if they seem unlikely to work. Post them separately, unless some other way would be more appropriate. If you've tried some idea and it hasn't worked, it would be useful to post that too.