Hello,
First thank you for responding, it's a tricky subject and I appreciate all the help I can get.
Now onto the topic :
First of all, the OpenVPN tunnel is not only a site-to-site server but a remote access one too (meaning sometimes I only want to connect to the OVPN IP, not the private subnets this machine has access to).
The tunnels are on a /20 but the LANs are on another, so no risk of collision. Our network plnning has been made to be a little future proof hence the /20.
On the PKI, good idea but no, maintaining it properly would cost more of my time than I can allocate to it, automating the renewal of a shared key is no big deal.
I was looking for a list of advanced options I can give to OpenVPN to assign a specific client-side tunnel IP belonging to the /20 in accordance to our naming scheme without letting the OpenVPN server choose it.