Figured it out...
I did not have an interface setup as a 'Management Address'. Once i entered the command: "set ip interface vlan.0.XX default" everything started working fine.
I'm hypothesizing that since no interface was setup as management, it was defaulting to the lowest interface IP address, which is a loopback interface...thus the reason why no TACACS+ messages were hitting my server.
I'm still stumped on why a ping would go through though. If the TACACS+ packets were defaulting to using the loopback (since nothing was defined), why wouldn't the ping use the loopback and fail?
Learn something new everyday...