Hi, Zuki...I've been doing that dollar volume for years, although that is not my main source of income. I'm just 80 miles south in Lexington, Lentucky.
Around here, it's not talent, but connections (thankfully) that secure the high dollar jobs. For most of my repeats, I have additional business connections via industry, the University or the horse business.
For me, it works both ways...I convert music clients to graphics/film clients and do it the other way around, too.
The difference between a $150 restaurant job and a $350 and up corporate or non-profit job is usually who you know.
I use a high end restaurant job to get the first contact. I work this one during the summer to book my better paying winter jobs. I actually make less money in the summer, due to the patio restaurant job.
Possible...YES! How long? Don't know!
Come down sometime. I used to play at the Blue Whisp....only a little more than hour from here.
Be Great to visit!~
Russ