I updated TurboTax Premier today and started a blank return to see if Intuit has fixed the issue. THEY HAVE NOT. I am disappointed because the program clearly does not behave as the Help/Instructions indicate, and more so since I've called, emailed, and reported this bug directly via the program bug reporting tool. Cass0317's reply does not address the issue, which is WITH REPORTING 1099-S (REAL ESTATE TRANSACTIONS) AND OTHER NON-1099-B TRANSACTIONS, not with 1099-B's.
I deleted the email reply I received from Turbo Tax - it basically said to navigate to Forms View, Schedule D, and enter the info directly, included the original post from DS30, but lacked sufficient detail to be much help. So, I ended up getting the program to correctly calculate the gain/loss on a real estate transaction (reported on 1099-S) by doing the following:
1) Go to: Federal Taxes/Wages&Income
2) Start (or update) the first item which should be "Stocks, Mutual Funds, Bonds, Other"
3) Choose "yes" when asked if you sold any investments in 2020
4) Choose "no" when asked "Did you get a 1099-B or a brokerage statement for these sales"
5) Choose "I'll enter one sale at a time" on the next screen
6) Enter description, date sold, date acquired, sale proceeds, and cost/other basis. Select the holding period (short or lonog term). Note that date sold and sale proceeds will be shown on your 1099-S. You'll have to rely on your other personal records to get the date acquired and cost/basis.
7) The next couple screens will ask about less-common items for the sale (market discounts, etc.), whether the sale was employee stock, and finally adjustments that may apply. For me, I had some fees/selling expenses to deduct and this is where I entered them.
Fortunately the calculation in my case was pretty straightforward so I could check the math quite easily. Basically take the sales price, subtract the cost/basis, subtract any fees/expenses, and that is the capital gain/loss. I didn't have any depreciation etc.
Oddly, the first time I tried the above steps there were references to 1099-B box numbers which didn't make sense. After I had manually navigating to Forms View/Schedule D, then gave up, when I went back to the steps above in the step-by-step view, I got the data entry boxes as I described in Step 6 above without erroneous references to 1099-B boxes. If you try to follow my steps above, and get something odd, try going to Forms View, Schedule D, then closing and going back to Step-by-Step view and trying my approach again.
Again, very irritating that we have to find workarounds for a minor program bug that should be easily fixed. When I spoke with a TurboTax specialist, she wasn't sure how to report program issues or who in her company to report them to - she was a tax specialist, not a program expert, and didn't know how to contact the program experts.
