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You will find the Form 1099-B entry in the Investment sales section of TurboTax as follows:   You enter investment sales in the Wages and Income section of TurboTax, then Investment Income. Update that section and you will see the investment sales that you entered. Click on the down arrow next to the investment you want to update and choose edit and you will see your investment entries that you can adjust as needed.      

To enter, edit or delete estimated taxes paid (Federal, State, Local) - Click on Federal Taxes (Personal using Home and Business) Click on Deductions and Credits Click on I'll choose what I work on (if shown) Scroll down to Estimates and Other Taxes Paid On Estimated Tax Payments, click on the start or update button   On Federal estimated taxes for 2025 (Form 1040-ES), click the start button   Federal estimated taxes paid are entered on Form 1040 Line 26

If the Roth IRA belongs to the beneficiary, they will track their contributions with Form 5498, and may receive a 1099-R from the plan administrator reporting the non-taxable transfer.  If that applies, you won't be able to or need to, enter this non-taxable rollover in your return as the recipient.   Here's more info from IRS Pub. 970.   @gigipanelli27     

Easier to post your question or problem here in the forum to get assistance.    Unless it is a billing question and then you must contact TurboTax support.  Use the key words Billing Issue Use this phone number and select TurboTax - 1-800-4-INTUIT (1-800-446-8848)      

At this time, the PTET election is not part of the Maryland state step-by-step interview in TurboTax Business. To add Form 511 to your Maryland Partnership return, click the Forms icon in the TurboTax Business header, then open the Information Worksheet and check the box for Form 511 under Part II. Proceed to enter all information needed on the form. Any fields in pink indicate a response is required.

There is no version of the software called "investments and rental property"----so we do not know what you have been using----perhaps desktop Premier or online Premium.     You will not be able to merge two previous TT account to start your new joint return.  You can transfer ONE of your 2024 returns into a new return, so choose the most complicated one.  The other spouse’s information needs to be entered manually.  The first name you enter will be the “primary” taxpayer——and in subsequent years you need to keep the names in that order—do not try to change the order of the names.     When you enter the primary spouse’s information in My Info, you have to answer the question "Were you married?"  If you click the button for Married, then a drop down will appear that asks, "Do you want to file this return together with your spouse?"  Then you choose YES to file a joint return.  You enter your spouse's information into My Info.  Whenever you are entering income information there should then be a spot for you and for your spouse's income information.  WATCH for the names as you enter income on the screens.  Or when you click to add income it will prompt you to choose which spouse had the income.   When you prepare a joint return you include all the information for both spouses on the SAME tax return.  Include all of your personal information, all of your income from every source, all dependents (if any), all credits and deductions for both of you.  You get ONE refund with both names on it.   And…keep a record of how to access the “old” account for your spouse in case a need comes up to print it or find information from it.  TT will save it online for seven years,    

Either version will work for you.   The Home and Business has everything the Premier version has plus more on demand help screens.   Home and Business is the most comprehensive product available and it will handle rental property activity.     Premier will handle his self-employment taxes but will have less help screens along the way.   But either product will handle both of your situations.       Is it better for a married couple to file jointly or separately?  (Jointly is almost always better;)

See this TurboTax support FAQ for how to use the Fair Market Value tool - https://ttlc.intuit.com/turbotax-support/en-us/help-article/charitable-donations-deductions/use-fair-market-value-fmv-tool-enter-donations

Response does not work.  I apologize, should have stated “… when using TurboTax DIY Free Edition.”     On my initial attempt to enter the transaction manually,  or upload the 1099-R, the results are the same: the process pushes the income to the 1040 Schedule 1, thus requiring an expensive upgrade to TurboTax in order to process this transaction.   On my 4th(?) attempt, deleting documents and entries, then reloading, the result is the same: a Schedule 1 display of the income, and requirement for TurboTax upgrade to process this transaction