#1
Would it be redundant to layer a more Fender sort of tone with a chimey Vox tone on a recording (or perhaps run the two tones in stereo live)? I've never really heard of it and I've been curious to get my hands on an old Fender Deluxe Reverb or Twin Reverb (if I can stand the output from the latter) lately. My downfall is that I love both Vox and Fender sounds and nothing quite does it like the real thing. I've also felt that although Vox can be make a great pedal platform for a variety of pedals and cuts through a mix nicely with those mids, an old Fender seems to just be extremely forgiving to a wider variety of dirt pedals. Comments? I'm not replacing my Vox, but I'd like to get some more options pretty soon. Price is whatever it takes to get it.
Fender Telecaster
DeArmond M series
Vox Night Train 15 head w/Weber loaded 1x12
Dunlop DVP3 Volume (X)
Klone circuit/Russian Big Muff 2in 1
Fulltone Fulldrive 2 MOSFET
TC Electronic Nova Delay
TC Electronic Nova Repeater
Line 6 M5
#2
Absolutely not. In fact, this is a common studio technique. Ever tried to obtain that same tone from your favorite recording and couldn't? There's a good chance they layered amps during the tracking.

FWIW, it's also quite common to record the guitar clean, then re-amp it later. Re-amping is the practice of playing the recorded clean guitar through one or more amps and recording the result on a new channel, or channels. How about that?