Justin,
I kind of hate when you ask me things like "What would Nashville think of this?" Kind of stuff. I don't have the vaguest idea. I can only tell you what I think, and what I've seen and overheard on these types of artists. He sounds very much like what a lot of people here were doing about five years ago. Now it sounds very dated to me. As the mainstream country audience has gotten more urban, the connection with this kind of music gets farther removed. This would be "your father's country music" and would be pretty much turned off by most of today's listeners who are going for Eric Church, Jason Aldeen and most of today's crop. He sounds very much like George Strait and while a lot of people are looking for the "next George Strait" I wouldn't be holding my breath for it to happen.
Music listeners go through a few distinct stages. They hear what is around them currently on the radio as they grow up. They hear their older siblings, their parents, etc. songs and get their own grounding in that, up until the early teens. Then they start finding their own music and ages 15-23-24 are spent looking for different types of music. There is a whole hearted rejection of anything they grew up with and that their parents or older siblings listened to. In Nashville, this type of stuff started fading about 5-8 years ago, and less and less of these acts got signed. So there is just not the groundswell of support for it. It becomes more "niche marketed." There is still a fan base, Texas as you mention for this guy, but it is not as widespread as the believers in this type of music would like to believe.
Today's country listeners have more in common with AC/DC and Aerosmith, than they do with any traditional singers like Strait, Jackson or Garth. One of the reasons Strait and Allen Jackson are performing less and less is that they want to go out on top and not see their audiences diminish like aging boxers or football players. They play less and become more "iconic" doing things like Vegas and Casinos, where their fans, who have grown past the arena days go.
We always hear the refrain of "That Ain't country" in the newcomers of country music. The older generation never likes to be replaced. But they always are. Just part of the cycle.
I am sure your guy will do well in Texas, which supports more diverse audiences. Here, I am afraid, is probably not going to embrace that style. But in an overall scheme he could be like Pat Green, who turned down a Nashville deal because "He couldn't take the pay cut."