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 does, legally speaking. Whether you would get caught and penalized is a separate question - First, brokerages have lots of reporting requirements, and likely would issue a 1099 or some-such to someone if there were a change in beneficial ownership of an asset. Second, the IRS has an all-but-declared policy of spending a dollar to collect a dime, purely for deterrence purposes.
In summary, aggressive tax techniques without expert guidance is asking for trouble.
Disclaimer to any reader: I am not your lawyer. I am not a tax lawyer. I didn't do any legal research. Don't rely on my opinion for any reason. Definitely don't rely on this opinion to try and pay less taxes. If this is a real issue for you, hire someone to do the research, or do it yourself.
I know nothing about tax law, so this is an important disclaimer. I won't end up trying this.
To spell out the idea, one could have their Roth IRA and their investment account at separate institutions. The Roth IRA broker would simply see a loss (gain) and the investment account broker would simply see a gain (loss). Each institutions reporting these changes to the IRS is the benefit of the finagling.
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.