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Ask yourself "if I was given the equivalent in cash instead of equity (e.g. a bonus or just an increased base), would I buy shares in my employers' company?"

If the answer is no, then it makes sense to sell immediately.

Diversification. If you consider that your employment at an employer is one part of your investment strategy, then it makes sense to diversify your portfolio as much as possible. Keeping those eggs in the same basket presents increased firm-specific risk .

Yup, makes sense.

I thought there might be some kind of specific tax loophole or trick to moving the money out of the ESPP. I'm finding more and more of these tricks as time goes on, such as post-tax traditional 401k mega-backdoor Roth money (if it lasts past this year), etc...

I've done this in previous jobs - nothing to do with the company itself, I just don't like tying both my investment and wage income to the same company.

I need the money now more than I need the potential increase in value sometime in the future.