So basically you're recommending a full-blown cygwin install over a ~300K standalone executable, and enable Telnet? And the GUI is only ugly for a few seconds, until you actually connect. Then it's a good old shell again. How about when I have to ssh into a server from a station I don't normally work at? You expect me to go out and install/configure cygWin so I can ssh? I'd be better off walking into the server room and sitting down at a hard-wired terminal. I know you can set it up on USB, but what if I forget that at the office? I can keep putty on the network/redownload it in about 5 seconds. Don't see that with cygWin.
cygWin is great, but if you are promoting it over putty for remote connections, then I'm not sure what you're on. If anything deserves the title of "best ssh client", it's SecureCRT, but you have to pay. Now, I can understand if you are living in a cygwin environment 99% of the time, but otherwise it's kind of pointless to say that cygwin is better than putty for remote connections.
Let it also be known that I'm a huge command line freak. My house server is commandline, and the linux server I set up at school is command line.