With Cygwin, your home directory should be your WINHOME (I'm doing this from memory, bear with me), so, in fact, your cd would be

    cd Desk<tab>bla

or, worst case,

    cd ~/Des<tab>bla

Running programs is also a tiny fraction of what bash can do - it's a full (well... almost) fledged scripting language and you can do things like loops, conditionals and other stuff. Before I discovered watch, I'd do things like

    while true; do df -h ; sleep 10 ; clear ; done

Also, the PuTTY-based console has a lot of niceties when compared to a plain console window - it's prettier, you have better font controls and better clipboard integration.