Closing deep ITM covered call position at a loss to offset gains on another position?

I'm interested in closing a deep ITM covered call at a short-term loss to offset short-term gains on another position. My investment thesis is that the shares involved in the covered call will remain the same or increase in value over time and I'd like to hold the shares. I recognize this is one major source of risk when executing this tax burden reduction strategy.

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My question is:

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The current covered call position is the result of a previously rolled covered call position (rolled both up and out). To 100% guarantee that I avoid wash sale rules, should I wait at least 30 days since the roll was performed? (And as a corollary, also wait at least 30 days after closing the covered call before executing another short position/covered call/call sale?)

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Is there anything else I should be aware of when trying to implement this tax reduction strategy?

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Other than the stock price going down after I close the covered call position at a loss, what other risks are there to this strategy?

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TIA for any insight - very much appreciated.