I wish I had a good answer for this one. I'd write a book and make even more $. I understand your struggle though and have gone through a similar process so I'll just throw in my philosophical 2 cents for what it's worth.
I'm a solo performer (singer/guitarist) and I do covers for a living. Mostly 60's & 70's acoustic stuff. It pays the bills. I'm trying to get more corporate and private work with slow but steady success. In Miami you can make around $125/hour like this, but it takes a lot of marketing (just like real estate or anything else). Bars and restaurants and clubs pay generally $150 for 3 or 4 sets if you're good, but it doesn't get any better than that and in the last 5 years has probably gotten a little worse. I'm putting together a home studio and then a CD to sell at gigs and online (you could probably give me the advice in this department.
Just in general I have had a hard time with focus. There are so many different directions and possibilities.
The only thing I could possibly contribute in terms of advice would be to live as simply as you can so you can do whatever you do to pay your bills in the least amount of time. Then take the time to think about what you really love to do more than anything, what you would be willing to focus on, make sacrifices for, and commit to for the long haul. Let your "day job" whatever that is (my "day job" is currently doing covers at night) support your passion. It has to be a passion I think because it takes time and is not easy. If it were easy lots of people would do it and then it wouldn't be valuable so it's a catch 22 if you know what I mean.
Once you have decided what your passion is then announce it to the world, and when it gets discouraging announce it again. Announce it to yourself in the morning when you get up and at night before you sleep and several times during the day. Get people to network with and know what you're about. I forgot who said it but there is a quote that you can accomplish almost anything, but you can't do it by yourself. Study and practice and focus on being the best you can at whatever you decide. You don't have to be the best in the world or even the best in Seattle. But if the people in Seattle feel that you are good and dependable and care about your work they will come to you. I don't know if I have the best dentist in Miami but since I don't have problems with him I don't bother to shop. Maybe a bad example with the drilling and all but you get the idea.
So the point is to decide and commit and focus on what you love. It can be a mistake to have money as the goal. I'm not sayin you should accept the starving artist thing, I actually think thats a bunch of bull****. Getting paid well for what you love to do is as good as it gets in the work department. And when you do something well you deserve to get paid well.
I responded to your post because like ole Bill clinton says: "I feel your pain". I'm not pretending to be some guru type but I've gone through a lot of this in 47 years and just now am starting to get that it's not money, it's the love and committment. And what do you know - I make more money than ever now.
By the way, with almost anything you choose it's a good idea to send out a newsletter every month or two. Mine is simple: a brochure format with some interesting jokes or quotes. People tell me they look forward to the newsletter just to read the quotes. In closing here are the two quotes from the last newsletter.
Best of luck to you
Bob
"Your passion is your source of power. To lead a really full life, you need to follow where it leads . . . in defiance of all things conventional, perhaps. And of course it is at a price. You have to know that going in. But the price you pay, in my opinion is not even worth the time of day to think about. It’s so important not to knee pad around the world. You should never bow down to anything but those you love and respect. Ever. For anything."
Doug Peacock
"Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. . . The moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred . . . Boldness has genius, power and magic in it. Begin it now."
-Johann Wolfgang von Goethe
