I think, at the end of the day it’s more about “what do I enjoy doing, and how can I get MORE enjoyment out of it?”
For instance, if you play golf maybe one day you want to challenge yourself to an open type course(St Andrews, Shinnecock) and see how you measure up. Cars? Maybe one day it’s your dream to own a Porsche or maybe a classic US muscle car, or in my case a soon to be bought C6-7 Corvette. Playing out in bars, festivals, casinos etc I could have cared less what I played through for the first 20 years of gigs. But the final 10 years I caught the gear chase bug. So now I get an absolute rush out of turning my amps up and letting it rip…puts a huge smile on my face. It’s for my enjoyment; as I’m a home player now. I’ve become a high gain tone snob in some ways, I know what tones I like and if I need to spend more to get it, I will. Sure, I’d have been fine playing my mini rack until this very day but I chose to chase down some cool gear, and it’s been a blast. If you are just as happy with your Mako as you think you would be with a Larry, good on you.
But owning gear has nothing to do with how accomplished a player you are….it just shows how much you like and enjoy gear, no matter your skill level.