"Upon looking more around in that area, I am going to report it as a summary and then submit the suggested and requested additional info (1099-B and spreadsheet) that will give better details on the overall transaction."
I really don't think that's at all necessary and I'd approach it differently.
First, when there's an actual "escrow" amount involved in a stock sale the IRS's guidance is that you include that escrowed amount as part of your proceeds in the year of the sale. Although the 1099-B made some distinction between "initial proceeds" and "escrowed proceeds", you don't really have two separate transactions, you have one sale with a small amount of time between the receipt of the money.
I'd simply report one sale using the first date, combine the two proceeds amounts, and enter the correct basis for your sale. The IRS's "matching" program, as far as I know, doesn't get down into the weeds and try to match each and every line that shows up on a 1099-B to a line you've entered on your Form 8949. If you report one sale that shows total proceeds that's the same as reported on the 1099-B from the broker I don't anticipate any issues arising on the IRS's end. The two different dates are irrelevant as far as your holding period is concerned and, more importantly, your obligation as a tax payer is to report your income properly and if you do that the IRS's really can't lay a glove on you.
