Hi Ed,
1) I recommend fill out Form W-4P for the state retirement plan and W-4V for the SS.
Form W-4P Withholding Certificate for Periodic Pension or Annuity Payments
https://www.irs.gov/pub/irs-pdf/fw4p.pdf
Form W-4V Voluntary Withholding Request
https://www.irs.gov/pub/irs-pdf/fw4v.pdf
For W-4V, you may choose to have the payer withhold federal income tax of 7%, 10%, 12%, or 22% from each payment, but no other percentage or amount.
Since this is your retirement year and there are many pieces of income data, please use
TurboTax Tax Calculator 2021 to pro forma tax year 2022
https://turbotax.intuit.com/tax-tools/calculators/taxcaster/
to see if you have paid in enough for the overall 2022 tax liability.
2) A rollover of a pretax retirement account to another pretax retirement account, in general, no loss is recognized and deductible since they are "pretax".
3) Converting from a pretax 401K to a Roth IRA is a taxable event. In general, a good time to convert is when the market is down (your pretax account has lost value), and /or you income is unusually low (next year when you only have retirement income), and/or you have a large itemized deduction.
Again you can use TurboTax TaxCaster to pro forma tax year 2023 to weigh the impact of the potential conversion.
Hope the above helps.
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