Unfortunately, I invested $26,000 in a company who is now worthless. It’s a long story but now it is official the stock we bought is worth $0, sad.
I am looking into my options for writing off the amount over time starting with my 2014 return. From what I have read I can;

(1) Write off $3,000 per year until the $26,000 is sufficed

I am wondering if this is my only option. The reason I ask is I plan to sell a rental home in the near future, which will gain over this amount in profit. I will have to pay taxes on this profit on that years return. I am wondering if I can wait and use this total amount when I sell my rental property?
Or – is it best practice to use the $3k amount, over time?

Thanks all!

Here is a snippet from Intuit.

"short-term losses are first deducted against short-term gains, and long-term losses are deducted against long-term gains. Net losses of either type can then be deducted against the other kind of gain."

From how I understand it, if the stock that you lost money on is classified as "long term capital loss" and the rental property is also classified as a "long term capital gain," you should be able to offset the gain with the loss.


I am NOT a tax professional. I suggest you check with a tax person to confirm my answer.

Source: https://turbotax.intuit.com/tax-tool.../INF12052.html

Here is a snippet from Intuit.

"short-term losses are first deducted against short-term gains, and long-term losses are deducted against long-term gains. Net losses of either type can then be deducted against the other kind of gain."

From how I understand it, if the stock that you lost money on is classified as "long term capital loss" and the rental property is also classified as a "long term capital gain," you should be able to offset the gain with the loss.


I am NOT a tax professional. I suggest you check with a tax person to confirm my answer.

Source: https://turbotax.intuit.com/tax-tool.../INF12052.html