I love Freedom to Fascism! I've seen it a few times and I'm a huge supporter of Aaron Russo and Ron Paul!
You can dispute each account separately, but it's really not necessary. If you do though, wait at least 30 days to send the second one, because if you send one, and then send one a week later, the investigation period starts all over and gives them extra time to verify the account. You don't want that.
I would never dispute more than 5 or 10 with TU or EX, but I have many times with EQ...because EQ always eventually ends up taking off whatever I dispute.
I have actually disputed up to 20-25 accounts with all 3 bureaus and I've seen 15-20 negative accounts come off at a time.
Some of our clients, if we disputed them 1 at a time, it would take years...by then, they would "fall off" the report anyway. I've had clients with 100+ negative items. One lady had over 80 tax liens alone.