[vtange]

Put options lose value over time. You are speculating on the near-term risk of stocks losing value - effectively trying to time the market/predict the weather.

Selling put options is a bet that the put options will expire worthless, which is a bet that stocks will continue to go up/not fall.

I honestly believe the insurance analogy for options is misleading. The value of an option is quite literally the difference in value between selling the stock at market price and at the option strike. As a stockholder you don't save yourself as much from buying put options regularly as you would from say getting a surgery covered with health insurance.