Has anyone dealt with stock option exercise timing?

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Illustrative scenario prepared by my practice.
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Hypothetical question

On mobile so apologies for formatting. Has anyone dealt with something like this? I'm not sure what my options are.

stock option exercise timing. I've been dealing with this for about 5 months now and the situation isn't improving.

I have already consulted briefly with a lawyer but got conflicting advice.

What are the risks if I pursue this? What's the likely timeline?