samb wroteMy goal is to be able to access a share located on the Server (on the Server machine, not the server-network).
Your configs show a standard tunnel setup, which means you can get access to a share on the VPN server .. although, you need to check your logs for errors.
samb wroteBut I cannot ping any of the remote sites (10.8.x.x) adresses from either server/client
If your logs show no errors then check your machine firewalls ..
FYI: In order to connect to a share you cannot use network browser, you must use:
net use x: //server.ip.address/share_name
