I make $15-20k a year but am still able to travel for several months and do multiple fests. I'm 26, unmarried, have no debt, do not want children, and don't want to buy a house. Since I'm living just for me it makes things much easier.
I am a test subject for drug companies and haven't had to work in over four years. I choose when I do studies which means I'm able to be free when I want to be. I never know what studies I'll do until a month or two beforehand. Sometimes I plan on doing a fest but find a good study and cancel my plans if there's enough money to be made. I had tickets for Sasquatch this year but ended up selling them because of that. The unpredictability is a definite downside.
I live within my means, save money, and travel very cheap. I don't have a credit card or ever spend money I don't have. I found a small, cheap apartment and have been driving the same car for over seven years. It is very fuel efficient and until it explodes it will be my car. I use the library and internet for my media intake. I own very little and put all my money into experiences instead of things.
I sleep in my car or with family and friends and never get hotels. I traveled about four months this year and based a lot of that around festivals or seeing my sister in Portland. I maximize the experience by doing things along the way like finding places to stop and hike at on my route. This way when I vacation I am doing more than just music. If you research a bit you can find tons of free or cheap things to do that are awesome. I don't mean being forced to go to a dog parade as your entertainment option. I only do stuff I really like and generally am able to do it for almost nothing.
At fests I bring my own food and booze so I don't have to be overspending. I really only spend for my ticket and the cost of getting there. I don't spend money on merch, lodging, etc. In Minneapolis I am within walking distance to all the music venues so do that instead of taxis or driving and then paying to park. I see multiple shows a month. I generally like to be sober for a show but if I decide to drink I just do it on the way there so I'm not spending on drinks.
Live music is really important to me and it's what I spend virtually all my money on. Jimmy John's get the second most from me haha. I guess I've just made fests/concerts a priority for me, and much like what many of you are saying, live my life accordingly so it can happen.