I'll be blunt, ssh is out of date.
If you post this in the linux section where it belongs you may get a better reply but IMO you would do better going to a Linux server forum and posting your questions there.
From a windows point of view, If I had to do this then I would make the Linux systems inside hyper-v and use the remote mag tool which is built in because that allows me to use a safe internet protocal to talk to my Linux machine and the Linux system doesn't know any thing different is happening because (as far as it knows) the commands are not coming over the [inter]-net.