Every position has risks and rewards, costs and benefits. There's no such thing as free money
If you ever think you've found it, asking questions is a good idea. If nothing else you can be confident that there are other bigger players, with more resources, that are looking for that free money and would have bought it all up.
In this particular case the primary limitation I see with a far DTE (days to expiration) position like this is that whatever margin or cash that is needed to back the position, it will be tied up for a long time. In this case, in theory, until Jan 2023 or about 14 months from now.
The other risk that I can see - that very low margin requirement is undoubtedly due to how far OTM you're at. $50/share margin for $38/share credit sounds like a pretty good deal. However if the shares start trading towards that $500 strike price then I would expect that margin requirement to be increasing. As one point of reference I sold some ~$1000 strike puts with a 1 or 2 week to expiration and needed $250/share margin for them. The closer to the money the position gets the more margin you'll need (up to $500/share - the strike on the option, or making it cash secured).
The benefit that I see with sort of approach is that we're in agreement that the shares are unlikely to revisit the $500 level, much less go below it. So it looks safe from that point of view. By selling very long dated options like this, you get some cash up front (positive cash flow is always nice) and you don't need to do any management of the position. You probably don't need to do anything more than you already do - keep an eye out on the strategy and execution by Tesla, and the occasional check on the share price. Weekly or even monthly share price updates is probably all you need. Thus low effort, low energy, with some money to spend up front.
For the rolling further out, I would think in terms of letting these options get much closer to expiration. The time decay on the option starts kicking in noticeably about 3 months to go, gets even faster at 1 month to go, and is really really fast the last week and last day. That time decay is where you earn (P/L) that income that you received up front. With a 14 month to expiration sort of option you mention I would think in terms of starting a new 12 to 14 month position every 2 months, but taking them (very close) to expiration for more like 6 or 7 positions.
Closing these positions with 3-5 months to go, I would expect that if the shares are trading at about the same price as they were when you opened, then you will have earned roughly $19 out of that $38. That's not bad but it took 3/4ths or more of the time to earn 1/2 or less of the premium. Your earnings will be heavily backloaded. Of course you can earn that premium faster if the shares are moving up.
My own view on this and it's not advice - I've sold 1 year puts and 2 year calls, and found that I didn't particularly care for either position. The problem was that the money was tied up for months to a year before I could finally resolve the positions favorably. I'll go out a month now but not further. That is also me with my objectives and my trading style, trading strategy, etc, and isn't something that you should adopt for yourself. It is input you can put into your own thinking, but we all make our own decisions and experience our own consequences.
Again NOT-ADVICE. Just things to think about as you make your own decisions.
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