If I have 1099-s from selling timeshare, what do I do?

You would enter this in your tax return using TurboTax Premier. The sale of a timeshare would be considered as a second home.

 

1. Open or continue your return
2. In the search box, search for sold second home and select the Jump to the link
3. Answer Yes on the Did you sell any stocks, mutual funds, bonds, or other investments in 2021? screen
   • If you land on the Your investment sales summary screen, select Add More Sales
4. On the OK, let's start with one investment type screen, select Other, then Continue
5. On the Tell us more about this sale screen, enter the name of the person or institution that brokered the sale
6. On the next screen, select Second Home (choose this also for inherited homes) or Land and answer the questions to finish entering your sale

• The drop-down boxes can be filled out with the details of the timeshare sale

1. Description - Timeshare address
2. Date sold - on 1099-S
3. Date acquired - from your records
4. Sale proceeds - on 1099-S
5. Cost basis - initial purchase price plus expenses of the sale such as closing costs.

Indicate if you ever used the property for business or as a rental. You are not able to take the loss on the sale if it was used for personal reasons.

 

Do I need to upgrade to a premier turbo tax to deal with the proceeds from selling my timeshare.  If anything I have a capital loss based on the original cost/closing fees and 15 years of other capital & replacement fees.  

No, 

as you say, it will be a Capital Gain or Loss. 

Don't enter it as a sale of your house, enter it under Investments.