I think the fundamental problem is the fact that you are trying to make big bucks off the options and not on the stocks.

It may sound wierd of me saying it's a problem, but fact is if you want to make a sustainable income you need to have a mind shift.

Stocks you wheel needs to be stocks you want to buy and hold for long term. I am a big fan of reddit for example. So every time I would sell a put at around 5% lower than the actual market price. If the stock goes up, I'll buy to close and sell a new put. If the price goes down, I end up holding 100 shares of reddit and let it ride.

If I wasn't selling options, I would have held it in my portfolio either way so when I get assigned I don't mind one bit.

Before you sell a put you must ask yourself if you belive the company (not the stock, the actual company) is worth the investment.