For me it's tone, looks, and playability. To some looks aren't important, but for me, if the guitar is goofy looking i dont care how good it plays and sounds, it's not going to speak to me and have me playing it for hours unable to put it down
Personally, I like mid 60's strats. I have played quite a lot of them down through the years. I like a Brazilian rosewood fretboard on a maple neck. I like vintage kluson tuners. I like a bone nut. I like a nitro lacquer finish. I like Grey bottom
Fender pickups. I like vintage cold rolled steel trem blocks. I like old growth wood that has already done all the warping, buckling, splitting, and bending it's ever going to do. I prefer alder bodies. I like vintage fender tone and volume pots. I like vintage capacitors. I like push back cloth covered wiring
Strats from from 1957 to about 1969 are awesome guitars. Not crazy about the 70's strats with the 3 bolt neck plates.
I have a 1966 alder body strat that I got for $150 bucks in 1976. Hands down the best playing and sounding strat I have ever held in my hands. Way above average when compared to all the other vintage strats I have played in the tone department. I don't know why it is but it is.
I have 5 amps and all I play through live is my 1968 drip edge Fender Pro Reverb. It's heavy but oh my God does that amp sound good.
If i set my 66 strat through the 68 pro reverb as a benchmark, everything else is *muh*