Does the program allow for the change in the tax filing status if a couple was filing Joint and then one of them dies earlier than the other?

If one spouse passes away before the other, the tax brackets change to single status at that time in the [...]

Is cost basis used and can I enter the cost basis for investments?

Yes, the cost basis is used for tax calculations if you are projected to spend down principal for taxable accounts. If the account is linked, the cost basis updates every day automatically. If you manually enter an account, you can enter the cost basis as you see in the screenshot below. src="https://cdn.livehelpnow.net/clients/21145/kb/cbas1_8a21f1e8-d126-404d-b95a-43a0280e84d9.png" [...]

Can I run Roth Conversion scenarios to see if it makes sense and the best timing and amounts for a conversion?

You can run Roth Conversion scenarios under Scenarios>Roth IRA Conversion. Most people run scenarios where they specify that they want to stay under a certain tax bracket. The program will show you exactly how much to convert in each year so you just stay under the selected tax bracket. You can also choose your own amounts to convert each year by selected 'Manual Entry'. View the amount to [...]

I linked an account but now want to unlink it for security reasons. I would like to keep all of the information that is there, such as the asset class, balance, etc. How do I do this?

An account can be unlinked permanently from Yodlee while still keeping the information. See the screenshot below. src="https://cdn.livehelpnow.net/clients/21145/kb/unlink1_975324ab-0386-4bb7-9fa4-589e2ebf3416.png" id="ad91bb69-7c36-4527-ac00-38b29cdfeb5c" alt="unlink1" width="90%" height="auto" data-image="ad91bb69-7c36-4527-ac00-38b29cdfeb5c [...]

Should the estimated amount from Social Security be used as the initial payment or should it be the SSA estimate less estimated Medicare payment?

The program estimate for Social Security does not include any deductions for Medicare. You should either deduct this from Social Security or put it in as an expense in the Goals & Additional Expenses [...]