I need to do some testing with 4.4.4 and it isn't available in my Android SDK Manager? Any ideas on what I'm doing wrong?
There is no problem at you Android SDK Manager, you just have to download the API 19. The API 19 is used by all the KitKat devices.
So in Android SDK Manager you should download the package below:
Android 4.4.2 (API 19)
It is going to work for all the KitKat (4.4.x) devices, including 4.4.4 that is a patch with fix/improvements from 4.4.
For further, take a look at the developer site about android 4.4:
https://developer.android.com/about/versions/android-4.4.html