@JJBraddock
Some general advice. tosdr.org might help you avoiding services you don't like. switching.software might help you find software alternatives. Choose Free Software apps as much as possible.
1 + 2) you can run a calender service on a freedombox. On Android you can connect it with davx5 and etar. On your desktop you could connect it with Thunderbird. This might not be as user-friendly or easy but it might be worthwhile.
3) maybe jamendo??? Not sure.