Thank you for the response. I think I will continue looking into Python - I've begun following the tutorial for C# posted above and it's definitely educational.
I'm not sure how far I want to go. As a sysadmin I work day-to-day on servers - 90% Windows, with Domain Controllers, Application Servers, File Servers. Outside of Server Administration I work with backup systems - Datto in particular, which is Linux-based. I also configure/manage networks - we have a spread of Cisco ASA's, SonicWALL TZ210's and Sophos UTM's. I also have to configure Layer 2 and 3 network devices - configuring alternate subnets and VLAN's.
Out of curiosity, I've figured out how to make a very basic website a few months ago - I host the server internally and configured the HTML through Dreamweaver. (www.dtammam.com for laughs). Programming seems like the next step - I have to script, and the logic makes sense - it assists me in automating tasks that would take hours to do. For example, one of our clients uses a CAD/CAM software suite - SolidWorks. I create an Admin install image, create a script that runs in the background and runs the image with silent parameters on each workstation. Took me about 2-3 hours to script - the install takes 30 minutes. 30 minutes times 40 workstations really saved a lot of time.
Programming seems interesting because the way I'm trying to enter it, I want to be able to solve little shortfalls that certain OS' and applications have. One example would be in the game Clash of Clans - I'd like to make a program where I have a field for each type of troop or upgrade, and if I enter how many troops or upgrades I'm running, it could give me the cumulative cost (the app isn't programmed to do it currently). I'd also like to make my own personal Dropbox-type service (this will probably require Linux programming with rsync).
The end-goal is to be able to see a problem and be able to create a program to solve the issue. It's hard to see the big picture for this idea (it might be ambitious), but I'm hoping my expectations are realistic!