One thing's for sure: boomers are still a majority of the population. You may need to get creative about finding them, but they aren't extinct yet.

Let's brainstorm ways to find boomer gigs

1) break out the phone book and make a list of organizations and clubs
2) send all of them a press release/letter introducing yourself, including a link to your songs online (or save postage and go door to door, handing them a flyer)
3) offer to play at their next function, and sell the sizzle. Talk about how live music brings more people, which means more sales. Enthusiasm is contagious.
4) places where boomers go, and there isn't necessarily live music, but there could be:
a) bingo
b) skating centers (many have a day set aside for older skaters)
c) flea markets
d) steak houses (definitely oriented toward country music)
e) pubs
f) clubs
g) book stores
h) coffee shops
i) rest homes
j) city parks & recreation, downtown revitalization often offer live music
k) any restaurant where the manager is a boomer (I've noticed that you can tell the age of a store manager by the music that is playing in the store/restaurant). Apparently you are going to places that are run by a different generation. Government bureaucracies and big business tend to have more seasoned employees making the calls.

the list could go on and on... but the phone book can yield surprising results if you use it. In business it isn't enough to HAVE a service you can provide... you also need to find customers, negotiate a fair price , advertise, please the customer etc etc. If you think of it as a business instead of as a hobby, it changes everything. In the eyes of your clients you immediately go from being one of 1500 bums looking for a handout to being an entrepreneur who has ideas and skills that can help them make money.

Notes Norton is a perfect example of a professional musician whose enthusiasm, pursuit of excellence and desire to please the customer put him wayyyy ahead of the rest who are competing for the same gigs.

https://www.dropbox.com/sh/ey71h8ep047758h/AAC12jNM0Hz9Q8zsh5iDeqNHa?dl=0