Remember that the actual max pain value is pretty worthless. It identifies the exact lowest point of this road through this valley.
View attachment 666800
What can be sometimes useful, and is nicely illustrated on maxpain.com, is large open interest spikes in puts and calls. Of course, they shouldn't be used as a primary analysis tool--as noted upthread somewhere, even big spikes in options still represent just a fraction of overall TSLA cashflow--but they can definitely enhance your analysis and increase the probability of your analysis being correct.
I usually do weeklies, so I'm almost always rolling them just a week out. I'll usually roll on Thursday or Friday, depending on how close strike is to underlying. If the contracts are far enough ITM that I can't roll up at least a strike in just one week I'll start to look to two week rolls and so on. But...often in that case of too DITM CCs I'll just let them expire and let my shares get called. I made my profit on the sale of the call; that was the point of the covered call anyway. That I missed out on more profit from favorable underlying movement is a scenario I accepted when I sold the call.
What day to roll is dependent on how ITM or OTM you are plus your future price analysis. First, if you're DITM and have little time value, roll ASAP because you're at high risk of early execution (BTDT). Next, if you think there's going to be a spike in underlying that would be unfavorable to your currently OTM call, close the call or let it expire this week to give your shares room to run next week.
If you have a really confident price target for next week that you can roll to now for (hopefully) credit, it
may be better to just roll now and lock in your analysis. Finally, and probably most likely, if you're close to the money or a little underwater, find the strike for next week that is a net-zero (or small credit) roll. Assuming that strike is below your price analysis for next week (= your roll will be suboptimal), compare your current contract's theta to that contract's theta. If next week's prospective contract has lower theta, hold. If the current contract has lower theta, roll.