I just thought I would drop in and say that the latest server runs well on macOS using the latest version of wine (https://www.winehq.org). It didn't work out of the box, due to incomplete implementations of msvcp140.dll and vcruntime140.dll.
Here are the steps I used:
install wine 3.0 for macOS.
copy the RAGEMP directory from your windows machine to your Mac.
copy the msvcp140.dll and vcruntime140.dll from c:\windows\system32 to the server-files directory of RAGEMP.
run wine and it will open a terminal with the PATH set up to use the wine binaries (they're not installed globally).
start "winecfg", go to the Libraries tab and add dll overrides for msvcp140 and vcruntime140 to load the native before the builtin.
finally, run the server "wine ./server.exe" and you should be able to connect to it with the ragemp client.