Butters, 275's with a decent sidewall height is the widest I would go on an 8.5" rim. A 265 would be my choice for your rims. I wouldn't think about running 295's on anything much less than a 10" rim, it just doesn't make any sense. And Nitto DR's will run just as good as MT's (which i think are the benchmark for DR's) but you do have to get them a little hotter.
Cole, I can't see you not getting any tire squirm and tread deflection with those tires on an AutoX course if you're really pushing the car. And you can't tell me that the tread stays flat during hard cornering either because i know it doesn't. Just because you don't feel it doesn't mean it's not happening. If you think they look good then that's really all that matters, but I think it looks hideous, almost rice (without trying to be insulting bro), but you have over an inch and a half of tire bulging out past the rim. And if you admit that it's not the "ideal" set up, why would you recommend it to someone else? I'm not going to debate with you about it because I think it's pointless, but I just don't think you should be throwing it out there as advice just because it "works" for you.
Running an 11.6" wide tire on an 8.5" is not solid advice by most peoples standards. Anybody else is going to tell you to get a wider rim if you want to run that wide of a tire. I run a pretty wide tire on my rim, but I also have 5.5" of sidewall. And I also don't claim that it is any good for cornering.