In thinking about this for my Challenger, I'd prefer to maximize the sidewall height and if possible have the same size at all 4 corners unless there's some advantage to having staggered sizes that I'm not aware of? So with a stock setup, would the 275/50/17 be too much at all 4 corners, or is it pushing it even for just the back?
A 275/50/17 is not going to fit in the front. You can get away with a 28" tire in the back, not always easy but it will work. But it flat out won't fit in the front. I wouldn't go taller than 26" in the front.
If you want to run a 275/50/17 in the back, you could run a 255/45/17 up front. That would be a 26" tall tire, and it will fit on an 8" or 9" rim, so you could go with the year one magnum's or rallye's.
As far as the staggered set up, the only real advantages are running larger tires in the back than you can in the front, and not having to wrestle really wide front tires with your steering. I run 275/40/17's on all 4 corners of my Challenger. The rears are a little short on sidewall, but it's really not that big of a deal. Its still a 25.7" tall wheel.
On my Duster, I'll be running 275/35/18's in the front and 295/35/18's in the back. I can't fit the 295 in the front, and I probably couldn't turn it even if I could. The 275 will be difficult as it is with a fast ratio steering box.