Is it really possible for Raul's quest to just dead end based on what you say to him after talking to all 3 characters? I even waited to talk to them all until after I had Raul join me, he had a conversation with me after each one and he never started up a conversation with me later about going back to his old gunslinging ways.

Maybe, It bugged on me when I fast traveled right away after talking to the 3rd guy. I had to re-lode then he talked to me.

From what I've read on the wiki that quest can be a hornets nest of bad choices. Do one thing wrong like learning the ranger takedown before I have Raul or killing Sterling to get his gun will make this quest impossible to complete. I always play it safe with this one and never talk to Loyal or the ranger before I have Raul. Talking to Sterling is fine since all of his relevant dialogue is repeatable.

Well hopefully they fix it in a patch with the next DLC. Would really like his upgraded maintenance perk.