Membership, Payment, etc

I’m setting up a website for a local Chamber of Commerce. I want to create a membership form where a new member can pay through Paypal, fill out the necessary info including pictures, etc., and then get reminded a month before the annual membership is up to pay again. IF they don’t renew, I want a notice sent to me so I can reach out. If they don’t renew their account should go inactive and all their content hidden, including calendar events they created, their listing, etc.

Is this pretty easy to manage? The plug-ins I’ve found don’t seem to say they offer all these features. Any advice appreciated.