Although this is probably quite frustrating, I’d suggest trying to test one thing at a time rather than several and you need tcpdump looking at every connection
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Are you getting the same IP in pwnbox as you get on Kali over VPN? I’ve never used pwnbox so I don’t know if that is normal.
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The TCP dump screenshot show traffic is flowing to your listener. If your listener isn’t seeing this is almost certainly down to something like a firewall or other ACL type control. It might be worth double checking that the listener was configured.
If you are on the VPN and you run python -m SimpleHTTPServer 80 or python3 -m http.server 80 then connect to http://localhost/ does it work?