I go with tone first, playability second, looks third. However, since many of my guitars were made for me I had to take a chance on tone. Being a guitar whore of sorts lets me accept all kinds of tones so I haven't been disappointed by my orders, though there are 3 acoustics I prefer, 2 Marc Beneteau and 1 Josh House. One of the Beneteaus is my accepted standard that I'm conditioned to measure others by, but I've certainly had my ears turned on by Thompson, Collings, and a couple of other brands in the past.

With electrics I prefer Strats and Teles mostly though I've got a weakness for semi-hollows too. Though I have others, my all time favourite "Strat" is actually a Godin Progression, followed by a Richmond (also a Godin) Belmont. My favourite Tele is a Fender Aerodyne (Japanese), followed by a partscaster assembled by Dave Wren (ex of The 12th Fret in Toronto), myself, and Josh House. My only semi-hollow at the moment is an Ibanez.

Lots of other guitars, but I easily narrow down my preferences by tone.

Peace, Mooh.