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?