Both guitarists in my band have £2000+ PRS guitars... I'm quite proud of being the member of the band with the cheapest kit.
I gig with 3 basses (not all at once mind you!), all of which cost me no more than £350 each, a Marshall "bitsa" 410 that cost me £150 (loaded with Celestion greenbacks! that was a nice surprise.) and a 300watt Hiwatt 115 combo that cost me nothing! (although an identical one sold on here for £100 a few months ago). I think I get a great sound out of my kit! I never get people speaking to me about my gear or sound, but I don't think I'd want to! Creepy weirdos!
The main time I'll check out a bands gear is if their sound is abysmal, it's all the more satisfying when they're gear is very expensive!
Case and point: I went and saw a band recently and the bassist had a horrible lifeless clanky trebley tone with no body and bass to it (in a classic rock covers band), he was using a David Eden 410 rig with a posh looking Warwick $$. Muppet.