#1
Do you think for around $800 my best option is a Fender Deluxe Reverb ReIssue? with maybe an overdrive pedal (is it necessary?).

I like classic rock, I like crunch for sure.. my number 1 concern is tone

I think I'd prefer an amp with onboard gain/crunch but I'm not sure
#2
I don't know whether that is a tube amp, but tube amps Overdrive the higher the volume goes , so unless you want to play distortion quietly, you don't need a pedal.
Quote by -BlackZeppelin-
Psh. I can can play fleshlight acoustically.

*masturbates*