@xokia well if you plug a device into your last switch in your lines port that is 23 untagged, or as cisco calls them an access port. And you don't get an IP from your dhcpd running on your vlan23 on pfsense, then yeah your missing something.
If you create a port on your first switch in your line that is in 23 UP (untagged, pvid) does it get an IP from dhcp? If so then do the same test on your 2nd switch in your line.. etc..
You mention your pfsense on VM, you sure its not stripping the tags? Been a while since I Played with proxmox - but VM software normally have to be setup to either not strip tags or put specific port groups or vswitches into specific vlan.. With esxi, I know you need to set the vswitch to vlan ID 4095 I think so that it doesn't strip tags.
I would test with that first switch coming off your proxmox -- put a port in 23UP, does it get dhcp from pfsense from vlan 23?