I've lived around Chicago my whole life, and I'll be honest, we have a little brother syndrome next to New York and LA that makes us pretty rabid about supporting guys that rep us. I've seen Cabana wrestle a few times locally now, and the love for him here is pretty off the charts. Its the kind of crowd reaction you want to get swept up in - but I've been unable to.
I can't speak very much to his ROH or IWA-MS days, but in the last couple years he strikes me as a fairly jaded, lazy performer. I'm a Chikara fan and I dig good comedy wrestling, but I've never found Colt's shtick to be all that funny or inventive. He bugs me, because seeing him up close he really looks like a guy who isn't even close to giving it his all. I really enjoy guys like Archibald Peck that wrestle comedy but stay inventive and work hard either in the ring or at completely inhabiting a character. My opinion is that Colt uses comedy wrestling as an excuse to do as little as possible. And his "character" is basically just himself smirking at the proceedings constantly. He's been very open about reigning in his work rate for health reasons, but there's a big difference between reigning it in and half-assing it.