I really like Conway and want him to win. Dude came from nothing, overcame hardships, health scares and adversity, and was able to start a rap career with old-school sensibilities and quality raps in his 30s - you don't see that often.
I do worry that he's going a bit far into the silly fits and fashion world. He's going for the Rick Ross old fly mob boss look, but it feels forced. It makes sense for him to chase some mainstream success but I like the gritty gutter shyt that he brought back on the scene when he came out.
I get that he probably doesn't want to make the same album ten times, but also hope he doesn't forget what made him popular in the first place