Good luck with it Al.
You are one of the fortunate ones in that you are familiar with the business side...there are many performers who are awesome musicians/entertainers/kareoke singers, but haven't a clue about how to run a business.
And, of course, you know that's the way it has to be done, if you want to make a decent profit, and minimize stress.
I did restaurant music for the past 20 years, mainly two to three nights a week, and carefully planned my repertoire and also all the details, which included the best type of speaker/amplification for that type of job, as well as a good sounding, and more importantly, reliable arranger.
In a way, I'm lucky I don't sing, and play all instrumental, because it is easy work...just have to keep adding new tunes, but always being ready to play favorites.
I made a very good living at it...enough to buy and pay off a house and several cars, as well as using the latest gear (only changed arrangers every so often...my speaker system was a one time buy).
Last year ,I decided to take the winter off, and now I'm considering taking this summer off as well...it really pays to put money aside so you can take a break if you wish, and not being forced to play makes a big difference in your attitude while you are working.
You are doing the right thing, Al...you are researching and asking questions, and most of the SZ'ers who are in the trenches can offer you much help and great support.
When you are doing what you love (i.e. playing music) it isn't work.
Ian
_________________________
Yamaha Tyros4, Yamaha MS-60S Powered Monitors(2), Yamaha CS-01, Yamaha TQ-5, Yamaha PSR-S775.