Christa,
I don't have much to add (you've gotten some great advice already), but I agree that your instincts and your analysis seems dead on. Trust your gut.
What happens when Richard is 24 and has a job, but he's "tired and sore" -- you think his boss is gonna care? no. It's the parents job to reward good behavior, but not with allowing bad behavior! Sends totally the wrong message.
And as for the car/bus thing -- if he really wanted to not take the bus, he would take the steps to learn how to drive, clear and simple.
And lastly, sending you BIG HUGS if I could I'd send a big ass glass of wine.