Funny thing, I've been looking for work for 2 years now and have found nothing despite being qualified and a great interviewee. I gave up on finding a 'real job' and have focused on music and am now making a great part time living off of it - and it's in an originals band, no less.
As a college kid soon to be entering the workforce full time, I'm actually going to spend the next 3 years focusing on music because there is more potential there for me than in the current job market. And this is coming from a double major in Marketing and Supply Chain with a 3.5 GPA, previous work experience, and an internship in my field under my belt.
Hey, you're like me almost 20 years ago. I graduated with a degree in business with a 3.6 GPA into a recession. (Sound familiar?) Job prospects were slim, and I had family issues, legal and financial problems, so I moved to Colorado.
Job prospects were bad out there as well. I got a full-time job while I got my music going. Things happened at work, I resigned and did music full-time. I was playing about 8-12 times a month and I was barely getting by. But it was OK, because I was barely getting by before. I didn't make much money, didn't get any savings, had no health insurance, but aside from the health insurance, my standard of living wasn't very different than before - crappy.
I did this for almost 2 years, and I did a bunch of searching, stopping and starting on various things in the meantime. At the end of my full-time stretch, the .com craze was happening and I found myself in a good job afterwards. Oddly, if it weren't for being in a band, I may not have had the skills to do the job as I learned a bunch of computer skills to build websites, promote the band, etc. which proved valuable in getting hired.
It's been more than 10 years since then, and even though I'm not playing out as much, I'm getting more per gig. I'm better on the business end, and I'm more stable financially which helps for getting your band promoted and equipped. I like my job for the most part, and it lets me do the things I really love - my family, my shop, and my music.
Your plan has some risks in it, but it doesn't mean it can't work. I'm a living example.