Routes are not to be mixed up with Firewall rules.
Firewall rules are for traffic that comes IN to an interface. pfSense is the "inside" in this point of view. Firewall rules do not apply to outgoing traffic (just forget about floating rules right now, themselves rarely being used)
To be sure that firewall rules are not an issue, put on any (V)LAN type interface a first rule that is a pass-all rule.
Routes : every LAN type network that is not declared as a WAN type can reach other because an (LAN's) network mask matches. If there is no match with an existing local network, then a WAN type network is used to send the traffic out to have the traffic being handled by an upstream router.
In the vast majority of all possible network scenarios, there is no need to manipulate the routing table.
I know, I'm probably not answering your question.
What I want to say is : routing tables is never a problem. They can seem to be a problem if the network structure is fckd up severely.
In that case the network's logical structure needs to be redone. Not the routing table.
Example :
Like you, I'm using the OpenVPN server build into to access my companie's nerwork.
My LAN is 192.168.1.1/24 - all companie's PC's, printers, file servers, backup units, etc are on this LAN.
A second LAN network uses 192.168.2.1/24
My VPN tunnel network is a third local network 192168.3.1/24 (and surely not 192.168.1.1/24 which will conflict with LAN - breaking the routing)
So, when I connect remotely, my PC @home will have a 192.168.3.2 IP.
Traffic going to my OpenVPN server comes into pfSense and can go
192.168.1.0/24 which is local
Anywhere else : the Internet, so it's leaving on the WAN interface.