system
A chat on subreddit /r/wallstreetbets
human
If that's your plan, you may want to consider buying an ATM or ITM LEAP call and writing OTM short-term calls against it to lower your cost basis. 
  
 Your strategy does work, but like you said, it strongly relies on market sentiment (over several months, since your date range is further out). If we have another February, you're begging just to get back even on OTM LEAPs. You won't be seeing significant moves on a daily basis.

gpt
Ok so buy ATM leap on $SPY and hold till November and close. Got it. 
  
 God I hate holding but that seems like a good idea. There is no way in hell that $SPY would be at $273.30 in November.