My most expensive is a '61 dot neck 335. It's not my favorite or my best...it was purchased in order to keep a chunk of change somewhere close by and "happy" for a few years. Basically...I felt there was nowhere better to put the money in terms of "preserving the capital" and that it may actually go up in value over the years. My next most expensive guitar is a '68 Les Paul Custom...some would say it's my best...and it's a damn good guitar...but I think my last Thorn, #39, is really my best in terms of of its construction, materials, tone, overall quality, its usefulness to me and the degree to which I enjoy playing it. Pretty much tied is the guitar that Ron made me just before that--my custom T-Caster.
For the most part, yes. The thing is, I like all my instruments and they all have their own nuances, which on any given day, I could have a new short-term favorite. In the end, I keep going back to the same number one.
My best is my least expensive,given to me by a good friend in exchange for a hand-picked case of good beer. And a bottle of Cabo-Wabo. This was my first electric and started this whole GAS mess, but I know that's the one that will always make the cut. Feels great, sounds great, and inspires good music out of me. What more could I ask for.