...I don't know if the TSA would have any "official" heartburn but I'd say, realistically, all they're concerned with when you pass thru security is that you have *a* boarding pass and a government issued ID.
You wouldn't have to show them both boarding passes.
Hell, they don't even read the dam things anyway. You could probably get thru with an E Ticket from Disneyland.
I think he's referring to the 30 minute prior to departure passenger list, not the TSA security checkpoint. Personally I'm not sure what the answer is, but my guess is that TSA doesn't care if you don't make it on a flight. They just run the passenger list through their database and that's it. You're non-rev so you can still get kicked off at the last minute anyway. So you can probably check in for as many as you feel like.