As a Kansan, I have to note that you've got the latin backwards from how it's used on the flag - 'Ad Astra Per Aspera'.

Have you checked out Statamic yet? Same principles as Jekyll, but I've found them much easier to use; better documented and with a bit more intuitive file structure by default. Not that you can't do that with Jekyll. Anyway, worth looking at: http://www.statamic.com/