Since both wow licenses are on the same battle.net account, the name should be available for you to use immediately if you delete or transfer “Bob.” It should only have the 30 day lock on the name for other battle.net accounts. I haven’t found anything that says that works differently on TBCC/Classic realms.
You may run into trouble trying to restore the original “Bob” later. Blizzard won’t allow the restore of a deleted character if you reuse the name as they don’t want players using that as a way to try and get a free name change, especially in versions of the game that don’t currently offer that service at all. You may have to delete the new “Bob” in order to restore the old one.
I know you’ve already transferred but I thought I’d cover this so the answers are a little easier to find for anyone searching.
If you delete the Shaman, as long as it’s on the same Battle.net account you’d retain access to that name on that Battle.net account and realm for 30 days (assuming the character is level 30+).
Technically, it’s two WoW licenses on the same Battle.net account so no, it wouldn’t. The phase WoW account is often interchangeable with WoW license, so it can get a bit confusing.
Since TBCC doesn’t have a Name Change service transferring or deleting the character would be the fastest way to make the name available for use.
Yes. Transferring is the same as deleting when it comes to how the server views the character.
On Classic Realms restoring a deleted character where you claimed the name it had for another character can be complicated. As we don’t have a name change service this circumvents that normal functionality so in order to restore the original character you may need to delete or transfer the character that currently has the name prior to undeleting the character.