I'm at the stage of thinking about moving some gear on but TBH I see a lot of my gear as a potential Life Insurance policy - gear I've acquired for not a lot which I hope to sell down the line for a bit more.
I have several basses I'll be reluctant to part with - the two that @Andyjr1515 built for me, my VC and the @Jabba_the_gut mini. While I'm still playing I plan to hold onto my Yamahas too.
I hope that once I've started to sell stuff it'll become easier.