Hi pacific_calm,
Aloha!
Thank you for your questions. Regarding the 11k+ tax bill, having more tax withheld will be helpful and avoid triggering the underpayment penalty. You can always put Additional Withholding in Step 4 (c) on W-4 for Extra Withholdings if you need. Our W-4 Calculator is a great tool to help you to find out if you need to withhold more so you can adjust your W-4.
https://turbotax.intuit.com/tax-tools/calculators/w4/
For your rental deduction, there is limit to offset the loss if your AGI is high and here is the link for your reference. https://www.thebalance.com/rental-income-and-expenses-3193476
For TSP to Roth, this article may be a good one to help you.
https://www.finra.org/sites/default/files/2020-12/thinking-about-rolling-over-funds-from-your-thrift...
You may give TurboTax a call anytime and we can review the impacts with you for each scenario.
Have a wonderful day and mahalo!
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