If I delete 1 Apple ID (email address) will the same email addy become available to use again?
The short answer is "Yes".

If you go to https://appleid.apple.com/ and log in the "Jim" AppleID. You should start by adding the "Ivan" address to the "Jim"  AppleID then make it the primary email address. Confirm that it works for logging in. Now delete the "Jim" address from the now "Ivan" AppleID.

Repeat the above for the "Bob" AppleID with the now freely available "Jim" email address.