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Good or bad time to head out on parental leave?
Any Carolina or Duke alumni in here?

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I don’t think so because I think they technically expire 12/31, even though they have extended to 5/31 the last couple of years
The policy stated roll over is only from 9/30 to 12/31
^^^ Good call @M1. California law states that accrued vacation can't expire because it is considered earned. Lucky you OP!!!
Probably not. Quit 12/31 then they have to
You live in California? If so yes, state law dictates they pay every last cent you earned
Only if you live in CA. Used to live in Cali so when I left my last firm, I received $$$ for PTO payout. If you don’t live in CA, you better submit your papers before Christmas if you want PTO payout.
Maybe
Is there a reason you're staying until January? Is it related to your bonus?