Rears are going to be real close. My understanding is that 275 is the biggest for the rear without having perfect wheel offset and a well centered rear end. Going bigger may require moving the springs inboard, which isn't hard. There is a sticky over on E-bodies dot org that has a lot of discussion and pictures. Probably had that discussion here before but it's not stickied. I do know that at least a 315 will go on the front and rear with nothing more than rolled fender lips, if you get the rear springs out of the way.
There are lots of onlinebackspace calculators that help you figure out what will fit based off what you currently have.
What is your rear gear ratio? If 3.23, for example, a 25.8" diameter will increase (theoretical) final drive to about 3.35 - - while a 28" diameter will reduce it to about 3.10. You can also consider same size wheels on all four corners - such as 15 by 8?
355 rear end...15x7 215/60R Front. 15x8 235/60R or 295/50R rear ... Haven’t decided anything for sure just wondering what this would look like... Painted steel wheels Small Mopar hubcaps
Car should look nice with either setup. Usually it's desirable to maintain equal diameters (front/rear) while possibly having more width at the rear. More rubber on road equals better traction - and handling. Taller on rear of course better than other way around. I've seen and heard plenty of horror-stories.
Even R-code (hemi) cars came with body-color steel wheels and some version of the factory dog dish covers. Keep in mind also that what looks super to the owner may not appeal to the masses out there. Ask family and buddies for advice also and possibly search and scroll on inter-web.
I don't know. I like the look of a full wheel well. I've got 255/70-15 on the back of mine because they came with the wheels. That tire is 29" tall. Looks pretty good in my opinion. I wish it was a 275 but the offset on the 8" wheel won't support that. These wheels/tires are temporary while I work on the car and will be replaced when budget allows.