Investors & landlords

Thanks so much for your response @Rick19744.

What you're saying makes sense; I guess the most confusing part to me is why the total of all the proceeds on the 1099-B does not match the amount of the liquidation distribution on the 1099-DIV.

My 1099-B is for Long-term Gross Proceeds, is a noncovered security, and the basis has not been reported to the IRS. It sounds like, although the Dates acquired are listed to me on my statement, this is merely informational to me and not reported to the IRS on this form, and in fact may not even be accurate. My statement indicates that the Date Acquired and Cost Basis have not been reported to the IRS, only the Date Sold & Proceeds have.

So to report this, I should:

1. Determine the total Cost Basis for all of my holdings as well as the various dates acquired. The Cost Basis can be calculated by looking at the FMV of the shares * quantity vested at each of the various dates. Compare this to the 1099-DIV amount so that I know if the sale was a loss or gain overall. 
2. Since each sale on 1099-B has been reported to the IRS, I must also include a line for each in Form 8949. In fact I only need to focus on sales reported in the 1099-B and not any others as these are the only sales that have been recorded.
3. (Here is where I want to double-check my understanding with you) for preparing Form 8949: 
   1. I must indicate a Date Acquired & Cost Basis for each sale on Form 8949.
      1. Date Acquired: The date acquired for each line was given to me purely as information, but in theory I can try to use this to locate the shares purchased on or around that date. (If there somehow ends up being multiple dates for the same sale then this becomes even more complicated and perhaps my strategy below will not work.)
      2. Cost Basis: To determine Cost Basis for a particular sale I need quantity. Since the quantity sold is not listed to me I must first determine that by dividing proceeds by sale price. Then I can take this quantity * FMV of stock on Date Acquired to determine Cost Basis for that particular block.
   2. Ordinarily in cases where the Cost Basis is more than the Proceeds, this will appear as a loss on the Form 8949. In cases where it is less, this will appear as a gain on Form 8949. However for this case if my understanding is correct, if the Cost Basis is more I still do not record this as a loss but rather instead make them equal since the loss can't be recognized until the last distribution.
   3. When I look at gain/loss, it seems that I need to be checking for each particular block, not the overall gain/loss (see my interpretation of underlined text regarding holding different blocks of stocks from Altaba below). Thus, even if based on my overall cost basis as compared to the initial liquidating amount I had an overall loss, if my research finds that for a particular sale I had a gain, I would still mark this as a gain and not mark the cost basis as equal to the proceeds for that particular sale, because the gain/loss is at the block level. Is this in line with your thinking?

A liquidating distribution received by a U.S. stockholder will first be applied against and reduce the stockholder’s adjusted tax basis in its Altaba common stock, before the stockholder recognizes any gain or loss. A U.S. stockholder will recognize gain as a result of a liquidating distribution to the extent that the aggregate value of the liquidating distribution and any prior liquidating distributions received by the stockholder with respect to a share exceeds the stockholder’s adjusted tax basis in the share. A U.S. stockholder generally cannot recognize a loss on a liquidating distribution until the final liquidating distribution is made, and then only if the aggregate value of all liquidating distributions with respect to a share is less than the stockholder’s adjusted tax basis in the share. If a U.S. stockholder holds different blocks of Altaba common stock (generally as a result of having acquired shares at different times or at different prices), gain or loss is calculated separately with respect to each such block. Any gain or loss recognized by a U.S. stockholder will be capital gain or loss provided the stockholder holds its Altaba common stock as a capital asset.

Does my understanding of all this sound correct to you? Thanks again for your help!