You list the cash in for both the person on whose behalf... and for the conductor. If there's only one transaction being reported, the amount will be the same and will also appear in item 25, 26 or 27, as applicable. But (for illustration) if you have three conductors making three deposits to one business's account, you list (again, an example) $5,000 on conductor 1's page, $5,000 on conductor 2's page and $6,000 on conductor 3's page, but the total of $16,000 on the business's page.
As for the multiple DBA names, the only technically correct way to file it would be to complete only one "on whose behalf" page for the CTR (the old Section A), and I'd list at least one of the DBA names. As far as I know, FinCEN has not offered a suggestion on what to do when there's more than one DBA name.
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John S. Burnett
BankersOnline.com
Fighting for Compliance since 1976
Bankers' Threads User #8