1) Yes
2) Yes
3) Yes, I can ssh from the ESXi host to the target machine and logon as root
4) all of the ip addresses are in the same subnet 192.168.140/24 (source machine .12, ESXi Host .14, and helper machine .16, standalone converter running on .239)
Source machine has an active listener on port 443 for it's normal operation (don't know if that's important, but thought I'd include the information).