I also think that both vintage and modeling have their places, although I think the place for vintage gear is a much narrower window than that of modeling. For myself (a recent college grad with very little money) the modeling avenue was the way to go. I can get all kinds of tones out of my Vox, and to me, they sound much better than I need them to at this point in my playing. While a good vintage Fender might be in a class of its own, I'm willing to sacrifice that little bit extra "class" to have a more versatile, affordable amp.
Leonidas' Gear List:
Electric Guitars - Agile AL-2800 (S.D. '59 B, Pearly Gates N), Squier Telecaster Custom (GFS FAT PAFs + Mods)
Acoustic Guitars - Crafter ML-Rose, Epiphone PR-350CE
Amps - VOX AD50VT, Epiphone Valve Jr. (Modded), Fender Blues Jr
Pedals - Crybaby Classic w/ Fasel Inductor, Boss DS-1, Digitech Bad Monkey, Danelectro Cool Cat Chorus, Danelectro Fish & Chips EQ, Ibanez AW7