I have multiple 1099 forms from the same brokerage. TurboTax won't let me retrieve the additional sets. How do I get around this problem with you software?

You may need to enter the other 1099Rs manually from the hard copy.   After you have logged in and are in your return in TurboTax Online:

• Go to Search at the top of the screen.
• Enter Form 1099-R in the search box. 
• You will see a Jump To function that will take you to the 1099-R input screens. 
• Then add a new 1099R and manually enter your 1099R.

At the financial services screens, click "Change how I enter my form" then "Type it myself"

This defeats the whole purpose of automatic download of the data, which eliminates data entry errors. Why do I bother with this software if I just have to enter the data myself?

The interaction with each broker, bank, and  issuer is different due to the different software interacting.

So, what you are saying is that TurboTax is working as designed. The problem is on my Broker's end. Would it be a simple matter to re-prompt for the account number like it did the first time and like it did last year? That way I can enter the account number I actually wanted to grab. Are you telling me that it's my broker's software asking for the account number? It sure looked like TurboTax to me.