Some great points so far. As I approach my own personal RE deadline, I will
1) Work through July of the year enabling maxing of all tax advantaged accounts including generally ineligible, with respect to deductibility, tIRA contributions,
2) Recieve full prior fiscal year bonus payouts,
3) Recieve full prior year portable pension credits, interest and funding,
4) Fully fund post tax Roth IRA rollover enabled 401K,
5) Ensure all vacation accruals have been fully utilized
My specific 401K plan ensures a "true up" with respect to matching, irrespective of service separation, end of each fiscal year for the maximum allowed match should the contribution minimum be met. Obviously, this requires the funds to still be a part of and subject to the plan rules. This would happen about a year later in my case. Funds are not required to be rolled out of the plan after separation from service though nominal fees begin to be assessed the account starting the first full year after separation..
This should result in some significant tax savings as a result and a nice boost into a future absent from W2 wages.