Okay, I thought that the Kenwood and the empeg were going into two totally different spots. If it's just a double-din and there's no difference between the two spots then yeah, it shouldn't matter which spots they're in.

Especially considering you don't have a tuner module, now I understand why you want to keep the Kenwood.

Trimming the dash opening to make room for a pull-out has definitely been done before, but it's rarely needed. If your car genuinely needs it, then go for it. Just be really careful and take your time to be sure it looks good. And make sure to get pictures.