Betting against volatility will *never* not be "picking up pennies in front of a steamroller".
Retail investors should not touch options under any circumstances, anyway. They're hedging tools for institutions and cannon fodder for day traders.
EDIT: I missed that the OP was saying to sell options for stocks already in your portfolio. I'll address that now:
I feel like this makes it even less worthwhile? Remember, black swan events happen once a month in trading. I think people would be really surprised at how far OTM they need to go to truly get to a "minimal" risk of their options being assigned. At which point the premiums are going to truly be pennies. If you're making any interesting amount of money off of a covered trade like this, it's because you're taking on an interesting amount of risk.