What are they? I am significantly past the OPs numbers and yet I can't figure out how to walk away from it. The health care alone is 30k (after deductible) per year unless you are employed and can get into a group plan. Once you add a reasonable cost of living, even in a cheap location, you get to numbers that are unattainable without a major stroke of luck.
Every strategy loses alpha sooner or later. The only real answer is to diversify your income streams - some money in the market, some in rental real estate, maybe invest into some smaller business. There are no miraculous strategies that will last you a lifetime. Apropos the OPs strategy. Short dates gamma is frequently rich indeed but you want to find these opportunities so don't do it blindly. Also, a large correlated move is the main risk, so either hedge or size accordingly.
It's easy to leave the rat race, not necessarily retire. Starting a company ensures you're only working on what you want to work on, with people you want to work with, and to some extent the hours you want to work. Don't get me wrong, you could very well still be working your behind off, but it's no longer a rat race. While risky, it's nowhere near as risky as most of what is postulated here and your skill and hard work have far more impact on success than it does in trading. Not for everyone, just like moving to the Philippians and living on $20K a year isn't, but an option most haven't seriously considered.
everyone's selling options until they get crushed-dumbest strategy ever. 16 years of successful trading have taught me to trade option strategies- I make money, my broker makes money,we sleep well. Selling naked is for utter morons! Options require education,stocks are also for idiots who have had dumb luck thanks to QE-and that will unwind sometime,and then all those weak hands will be selling their $100 stocks for pennies. Look at a chart of the S&P and learn!
Everything in the market is basically priced accordingly, more or less, to the risk/reward profile. -- I kind of prefer to call it a Skill profile. I wouldn't necessarily call one strategy 'dumb' over another. (i'm not defending this or trading this -- just being objective about it)
If this happens, why not sell ATM covered call verticals instead? You'll still get premium income, and you keep upside potential with the long option. You lose the upside equal to the width of the spread, but once the underlying gets above your long strike you're golden. I can see this being a problem in choppy markets, though. The upside you lose due to the width of the spread will be sorely missed when the underlying goes back down. Any ideas on how to mitigate that part?
Somebody has to sell you that spread. If it's systemically unprofitable for them, which it must by if it's systemically profitable for you, they're going to stop selling it. So there is no magic combination of options that will consistently be profitable for you over a long period of time. There may be a corner of the options world where options are mispriced, that's what we're all on the lookout for. But it's probably not going to be through the way you combine ever more complicated groups of options.