Investors & landlords

The "work-around" is pretty labor intensive. You can enter groupings of transactions as long as you don't exceed the $9,999,999, but the groupings may not always coincide with the summary totals. I was able to do this with a spreadsheet and entering each transaction and then totaling groups of transactions under the limit, but if you do this, you need to include your spreadsheet with your return and the copy of your 1099-B, so your accuracy can be verified. If you are dealing with hundreds of millions of dollars worth of transactions, this will take a significant amount of time.