On a few of the cheaper switches I have used, VLAN with an ID of 1 can only be setup as a native vlan and cannot be tagged on any port that it is configured for. In your picture "VLAN 1" is setup as a tagged VLAN for pfSense. You did not mention what the VLAN id of VLAN 1 is.
I have had consistent results when creating trunks between pfSense and layer 2 devices when all the networks that pfSense needs to talk to are tagged and there is no traffic on the untagged VLAN.
Some switches that I have come across can only bind their IP stack to the untagged only VLAN with id=1 particularly some of the cheaper Dell switches. So I normally keep VLAN 1 exclusively dedicated for switch management traffic.
If you want to communicate on a trunk between pfSense and a switch with both tagged and untagged traffic then for the untagged traffic you will have to add the raw interface "re0" (just like you have re1). Then for the tagged traffic add a VLAN from the VLAN tab and make re0 as the parent interface for that VLAN.