Does it make tax sense to sell a portion of my vested stock options to pay debt or will this sale only create larger issues for taxes next year?

[HelenC12]

Yes, it depends how your stock sale will affect your tax return and if the benefit of the sale exceeds the debt and/or cost of having the debt.  You can use the 2022 TurboTax software to do a "what if" and get a good idea. Create a new TurboTax account and enter your 2022 income tax information. Then, enter the stock sale to see the tax ramifications.  

[RJH23]

Can I do a “what if” with the online version of my current account, or would I have to create a new account?

[xmasbaby0]

@RJH23 

Online TurboTax does not have the "what if" feature.   That is only a feature of the CD/download software.  Do NOT mess with your own 2022 filed tax return that you prepared using online software or you will destroy it.    And...sorry.....it is too late to "start" a dummy 2022 return now.  The deadline for starting a new return using online TurboTax was on October 16.   Now you would have to wait for the 2023 online software to become available in late November/early December if you want to use online for any sort of "what if" scenarios.

[NCperson]

@RJH23 use this website to play "what if" 

https://www.dinkytown.net/java/1040-tax-calculator.html