If you are serious... Pay them a regular living wage... Remove the whole caveat that waiting staff is somehow different from any other job.

Fairly certain you can no longer talk to a merchant now with one character and them rob them blind with another. Bummer

Edit: not sure what happened, but tried a different merchant and it worked. I couldn't do it at the grove blacksmith guy after the patch, but I could before.

You don't hear a good bloodhound gang reference often.