Yeah, timing on entry points surely affects the comparative returns on MSTY vs MSTR, but my suspicion is that on average MSTR performs better than MSTY over most time frames.
If however I choose the 2024 high for MSTR (11/20/24) as the start date of a comparison through today, than the MSTY edges out the return of MSTR. And if you look at the worst performing period of MSTR (11/20/24-04/08/25), MSTY also performs better
So small sample size, but it appears that when the underlying is moving bigly, and IV spikes, the options selling ETF performs better than the underlying. In periods of normal low volatility, the underlying will probably always performs better. Which makes sense because the options premiums the ETFs can capture are lower.
Ive been trying to mess around with ChatGPT more to automate shit, so I spent a bit of time this afternoon building a model that allows me to dump price data, dividend data, volatility etc... and have it compare returns assuming dividend reinvestment. Now I can dump in data from a lot more of the options selling ETFs to see what shakes out. Is there an IV sweet spot for the underlying that starts to throw the advantage towards the options selling ETFs? Its really more just an exercise to practice using AI and I'm not expecting to learn much more than higher IV = better performance on the ETFs.