Right, so I've gotten all three bits of conversation from Raul after talking to Ranger Andy, Corporal Sterling, and Loyal, but during the last conversation, he ends with the line about how he's always had his doubts about giving up gunslinging, and realizing that from traveling with you, but instead of continuing the conversation into the dialogue where you can convince him to become a vaquero or a better mechanic, the conversation just ends.

Is there a reasonable workaround I might be able to implement via the console? Just like, a completed quest flag or something, doesn't matter, so long as he gets upgraded.

The same thing is happening to me, also two others on the vault wiki are reporting this bug. a fix or workaround would be great.

I was able to turn him into a vaquero via conversation options with no problems. However, I had to initiate the quest via the console since Ranger Andy had already taught me the take-down move, so I wonder if this has an effect on setting any progress flags. Did you start the quest via the console or normally?

On a side note, is the vaquero costume lootable? When I play through as an evil bastard next time, I hope to pop Raul and rock the vaquero suit.