So I have a few private keys I generated for Public-Key SSH authentication. In Windows I manage SSH keys with Pageant - an SSH authentication agent for PuTTY. PuTTY is an awesome SSH/Telnet client for Windows that also comes with a suite of helper utilities like key generator and agent.
My work week starts like this: I log into my Windows workstation, open Pageant and load my keys one after another. Since the keys are encrypted I have to enter a password for each key. Once the keys are in memory I can securely log into multitude of Linux servers (that have the public key) without enduring their login prompt each time. Pretty nice, but there is still some room for improvement.
