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Never been there but I I imagine it must be less glamorous after a certain age unless you make it. These days, there's no more making it in that sense, I guess.I tried it in my younger days. Managed a music store, taught guitar, and gigged 150+ nights a year. Way too much work for way too little money, and this was long before the internet so there wasn't even the option of being the condescending, hot shit "I do this for a living" know-it-all.
In any case my first post was meant to touch on the idea that it's more about the playing and less about the number of amps and cabs. And for the second, yes, I do believe that buying a digital box thinking that you'll get the same as the guy who paid in different ways by being forced to use an amp is impossible. And by getting the same and paying I don't mean anything related to tone. All effort is recompensed whether that is being forced to use one amp and knowing it inside and out, having to carry heavy gear, spending 10 hours of day practicing when other people are out dating, living the musician life and getting through hard times when you could do something else etc.
And I also believe that someone who is comfortable is most areas can't really do music. Something needs to give ...