I just got a new OpenPGP key from someone. His old OpenPGP key was outdated.
After I had added the new key and verified its signature and told TB about it, I still was not able to use it: I got an unspecified error message "Versand fehlgeschlagen!" or similar.
The maze was over, after I had deleted the old public key (which even was outdated, bit I did not check if that actually plays a role).
So I propose to check the encryption key's database when adding a particular new key if there are any old or even outdated keys associated with the to be included new OpenPGP key. If this is the case: offer to delete the old (and possibly outdated) keys if they would otherwise prevent TB from actually writing encoded mails to the particular email address and tell about this, e.g.:
"Key ID=.... associated with the same email address .... (if applicable: which is outdated). The presence of this key would prevent the OpenPGP key to be added from being used. It does not make much sense to keep the old public key, since you are now adding its successor. Do you want to delete the old OpenPGP key from the key database?"