ssh is a protocol that is used to log in to a computer remotely. Servers are usually administrated not by plugging a keyboard and monitor into the server, but from another machine via ssh. You can configure ssh to allow login with the same username+password you would use locally, but it is common practice to only allow authentication with an ssh key.
ssh keys allow for much higher entropy like you suggested. They are also asymmetric, and the private key can be password-protected or stored on a smartcard.
If you rely on some specific piece of software, set up a dual boot and only boot into windows to use that software. Put your Linux installation onto a separate (encrypted) partition.
We're never going to solve the chicken-and-egg problem of user adoption and software availability with the mentality to only switch once everything works 100%.
I know computers are hard for normies, but I believe that's only because they've been using dumbed-down walled-garden stuff for too long. And just like it is important to know how to cook and do basic repairs around the house, a basic grasp of computers should be the standard in today's world.
Es gibt dutzende von uns, dutzende!