1. What is the advantage of doing LEAPS out to 2030 instead of staying with 2028 or 2029?
Theta decay would become an issue with 1 year or less before expiry.
The initial investment is larger if going out to 2030 vs. staying with 2028-2029.
The only benefit that I can think of going to 2030 is if SPX will start declining.
You would still have to roll up in case the SPX will keep moving up, so why not get the maximum return on your investment by staying in 2028-2029?

2. I understand the reason for keeping uncovered LEAPS. You can get much higher premium if you catch SPX in a down move. However, does the math works? If you are waiting for 3-5 trading days, then the premium lost would be $30-50 per LEAP. Do you think you can get that much in a down move in SPX to counter the lost revenue?
Of course, if you are holding uncovered LEAPS just as a hedge, then my question is irrelevant.

Would love to know what you think about this.