Well, I can't recall whether anonymous Visa gift cards were available in 2007-2008. If they were, and this super-private guy didn't explore the option then he's not very careful is he?
All communications of the Satoshi Nakamoto inner-group were behind online pseudonyms, so it was rather unlikely that these people were in the same city. Still, the paranoia is part of what makes the Bitcoin origin story fascinating.
Ep. 94 - A Satoshi Nakamoto Story | Phil "Scronty" Wilson
https://www.youtube.com/watch?v=_OPCVeo1u20
The guy is a super nerd and he's terrible when talking to people. So the story is excruciating to get through, but there's a there there.