Although I've never had expensive gear, it's not to say I never wanted to have some.
There was a time, about 5 years ago, where I was going to save as much as I could for a 4 figure £'s bass, a cab from someone like Vanderkely or Barefaced, and an amp that was equally cool/hot/expensive.
However, apart from never really having that sort of money available even if I saved and saved, combined with that I've never really played enough to justify the expense I also had a bit of an epiphany moment. A band I was in supported a very well known local band one night. The bass player played a Squier Affinity P bass. These guys did maybe 200 shows a year. He also let me use his amp and cab, a Behringer head with a 112 cab that looked like it had been dragged behind a truck. I just thought, I need to get my priorities right...which was I had decent gear but I don't practice enough