Static Routing changes
SO, I got all busy screwing around with my static routes under "System", then "Routing", and screwed up something bad with my VPN.
Quick question, do I need to reboot the PFSense box every time I make a change to that, or is it good to just keep fooling around with it?
It depends on what you did. If you added a static route that overlapped something used by another service such as OpenVPN, then removed it, you should be able to save/apply in the relevant section that originally created the route to get it back. In the case of OpenVPN, just restart the VPN with an edit/save to bring that back.