I've got a few guitars that either started expensive or became expensive over time. But they're sentimental to me and I'm happy to keep them and pass them on to my kid who plays.
In terms of nice gigging axes they seem to run about 4K plus a few hundred in mods these days new. If I can find what I want used I will. Rock/Metal/Mixed gigs I use a KE2 with EMG 81TW/89. Country I use a Warmoth bender tele I assembled with T52s and a boost circuit, which was cheaper. Jazz I use a Heritage Eagle.
I also have a BCR USA Mockingbird, which was expensive. I love it and use it in the studio some times but it is sort of too expensive - I don't like to gig it.