Cash settlement eliminates the risk of early exercise and pin risk. You never have to worry about whether or not you will be assigned. This can be a big plus, although if you are long these options you won't have the opportunity to exercise early or after hours on expiration.
I was more looking at if there is an opportunity of buying cheap otm options at the option close, then rely on the underlying to push them into the money (or not) and just rely on automatic assignment. I’m still trying to understand the rules.
I'm not sure if there's a time gap between option close and expiration
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