For Kenton City Schools our original domain name was the standard
kenton.k12.oh.us. Unfortunately, only techies could remember it
correctly, so I registered kentoncityschools.org.
I’m still kicking myself for not registering the .com version, it’s
since been picked up by domain squatter. Kentoncityschools.org has
served us well, even with it being longer than our original k12.oh.us
version.

In the back of my head I had always wanted a shorter domain, and with
more and more mobile technologies being put into use, it only made sense
to try to find a shorter domain name that we could use to supplement our
current two. Trying to find a shorter .com/.net/.org was futile, so I
started looking at alternative top level domain names, and settled on
kcs.me. Now you can go to http://kcs.me/ and it will
automatically redirect to our main page. I haven’t started integrating
it into to many other services, but I do plan on setting up our email
accounts so you can use @kcs.me for any current address and it will
work. We also have a custom 404 error page that let’s us setup keywords
as shortcuts to commonly used web pages on our website, such as the
user’s personal portal page (their MyCatPage, kcs.me/my) and staff
home pages (kcs.me/collinsr).

For your school or business, have you thought about additional domains
or am I just being weird?