Can you prove that you are able to connect to port 9100 on the printer's IP address? I'd use tcpdump(8) with telnet(1) or nc(1) and confirm you complete a TCP 3-way handshake. This looks like a networking issue, and I'd suspect your PF configuration of being the root cause if you cannot establish a connected state.
Logging PF blocks and passes will also aid your analysis of you cannot establish a connection to destination port 9100.
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