A response to my last inquiry about the loss being claimed on my taxes has been resolved. I called this morning and talked with a very helpful rep who said "I taught him something too". Bottom line: Turbotax did not do any justice in helping its customers with the 1099-S form for the purpose of selling a second home. In the past, it has provided a very helpful wizard to walk through and then taken care of the background details. Not this year. It was moved to the Investments area where stocks, bonds, and mutual funds are heavily catered toward (even substantially in the "help" area). The process in now bifurcated as well. For example, I took an overall loss on the sale of the second home. The old wizard used know, based on first the availability of a selection of a 1099-S form (which is missing) that it was for a sale of a second home (also missing) so the software claimed my loss. While there is an option to make a checkmark by the list of later options provided not to claim the loss, the customer would have to know first that the loss could not be claimed for a second home...if they didn't they would leave that and receive an inflated return amount. This type of situation was taken care of previously in the background when the customer would identify that it was a 1099-S with an option for the sale of a second home. This (of all years) to be handled this way in a year of record-low interest rates where homes have been selling. This has nothing to do with the worksheets...that happens every year when the IRS has not finalized on their side. This has to do with the software and the wizard that used to exist to take care of the customer's need to file their taxes properly who shouldn't have to know these important tax details and then have to make the appropriate selections in order to have their taxes filed correctly. It was good before...why break something that was working just fine? The person who was very helpful on the phone today understood the shortcoming. After all, as identified above by anther member, the self-employed version retained the old method. This needs to be fixed and I hope this helps someone else after I have spent literally hours on the phone with Turbotax reps and "escalated" reps trying to figure this out this year and get this resolved.
