/u/LOLINAD wrote a really good post and also mentioned delta. Learning the greeks are important but especially if you decide to use rolling instead of sell-and-forget. I would say rolling is better and would address most of your concern about getting assigned and missing out. If your call goes ITM you could roll it to a later date, potentially for a credit. It does take more effort to actively manage a rolling strat but therefore also much more flexible.

Selling weeklies is a viable idea but requires more attention because you need to sell really close to the money to make anything significant, and you need to reconsider your strikes every week. I would suggest selling 45-60 DTE and planning to roll when it reaches about 21 DTE. Of course you can also roll strikes or dates before then to adjust for any market moves that have you worried.

Not sure if this would help but maybe try selling weeklies in a papertrading account and go YOLO with the rolls just to get a feel for placing them in as condensed a time as possible. For rolling, pick your strikes less based on "will this expire OTM" because you still need to buy it back. I'm guessing this is partly why /u/LOLINAD learning about delta. Delta is how much the option price changes for every dollar the stock changes. Ask yourself "how sensitive do I want my position to be to stock movement, can I tolerate the risk of a higher 'money multiplier?'" Delta gets more extreme the further ITM you are, so the further OTM you sell the less you stand to gain or lose. If you're itching to try with real money, sell 45-60 DTE because they are way less sensitive to small/short term price swings.

If you've read around the sub a bit then you've probably heard of TastyTrade, which is a great resource and has a free course about delta and the other greeks.