What kind of music will be played with what kind of guitar? That's really the basics of where to even start looking.
I've got several different kinds of amps and guitars. From a early 90's Epiphone Les Paul to Paul Reed Smith PA SE. Peavey 5150 combo for hard rock to the dreaded early 70's Fender Silverface Vibrochamp. Nothing pricey in my arsenal.
What I really want is a USA Strat with a Fender Tweed Deluxe (or 5E3 clone) for blues.