I haven't owned too many guitars and have only owned one electric at a time. If money were no object, I probably would own a bunch of vintage instruments, but I really only need one.
As a teenager, I started with a shitty department store Harmony or something. Then I bought a Fender Music Master - that was pretty lame. Then in 1985 I sold it and bought a Japanese Squire strat. That thing was great. I wish I still had it today. I always wanted an SG though, and when I found a 1968 special in 1995, I sold the Squire and bought that. I haven't bought an electric guitar since.
I'd still like to have a fender type deal too, but I can get a lot of different sounds out of that SG, so I'm pretty happy.