Does your Club have status as a legal entity?
If it is a legal non-profit and you want to start presenting shows with an entry fee and paid performers, you should have liability insurance to protect the BOD. As far as paying performers, anything under $600 you don't need to do anything. Starting at $600 you need to get a W9 from the performer and issue them a 1099 at the end of the year.
Then there are house concerts. There is quite a bit of grey area there, and many people hold them with no legal status and just keep everything on a cash basis. It's unlikely that the State of Federal Govts. would go after you for the occasional house concert, but without liability insurance the homeowner would be on the hook should anyone get injured on the property.
Scooter