Hi @mahoganyPT
Thank you for this question, it looks like there is a lot going on this year! You are taking the right steps by selecting the box on line 2(c) of your w-4 form to ensure enough tax is withheld from each paycheck.
The most important thing to remember is the amounts withheld from your pay slips will be summed together to determine a total amount withheld when it comes time to file taxes. So, the objective is to estimate your overall tax due for the total income you think you will receive by the end of the year and ensure the total amount withheld matches your estimate. That is much easier said than done, as you have already discovered. So, I have added a link below for our W-4 tool to help in the process. This tool will help to estimate amounts received across multiple incomes and apply the appropriate tax percentages. Use the tool to review your circumstances as well as hypothetical circumstances.
The IRS also has a tool that may help, so I have also included that link. The w-4 is somewhat of an art, so once you make changes you may have to update a couple more times to dial it in perfectly.
Good luck and have a great day!
W-4 Calculator - Free IRS W-4 Withholding Calculator 2021-2022 | TurboTax® Official (intuit.com)
Tax Withholding Estimator | Internal Revenue Service (irs.gov)
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