Hi,

LAN rules aren't important, as initial traffic goes out the LAN, not coming in.

"VPN"(or, if absent, "OpenVPN" tab rules) rules are important :

0_1536296717294_ef132e19-b33e-4ea1-8446-ed0be1b97912-image.png
do you see the state counters going up ?

And, as you didn't mention : some other little details, like the local LAN from where you run your Mac with Viscosity must be different as the remote LAN on pfSense with OpenVPN.