These questions are geared towards amateur musicians and listeners.

How many clubs do you know for listening to good music?

Probably 20-30 or more. Not 1-5.

How many live events do you attend per month?

Zero. We're always booked (or were before the quarantine). When you play over a dozen gigs per month you don't have much time to see other bands.

Get in touch with the booking agents in your area. Get through the gig and get paid. I don't see how an app would help with any of this. In my area there are three major booking agents you need to work with. Only a couple venues handle booking music themselves these days. You just work with the agents and get booked. Done. Most musicians and bands don't carry the right kind of insurance to do it all themselves either. Also, in any scene there's gonna be a handful of regular venues known for live music. It's not a mystery.

Your questions should be more inclusive to people that do this for a living. You'll probably get more insight into the process.