I tried to teach Speak/Quiet together, but had limited success. He has to get really worked up to bark on command, so usually I have to give him the command several times in a row. He knows what "Quiet" means, but uses his own judgment on when silence is appropriate.
We also definitely went through a period where he "offered" barking behavior a lot, because if I would command him to do it, I must enjoy it, right?
I think he just can't quite believe that I don't want him to fend off all the terrifying people/dogs/mailboxes that we come across. If I'm sitting in my office and someone comes in, he'll bark very menacingly, even if he knows them. Then when I tell him Quiet, he starts whining and making odd yorkie noises. I'm pretty sure it's because the urge to defend and the urge to obey are too much for his little brain to handle simulataneously.
Anyway, please let us know how it goes -- I'm very interested to see!