I finally figured out my environment issue with a little help. I ended up running this command
gem pristine --all to clean up my gems after the OS High Sierra update. Worked like a charm, but took a while to track down the issue as a whole.
I also started a side project over lunch. The domain <a href=snowmaha.com >snowmaha.com</a> was available so I bought it, stood a Sinatra app up, and utilized some css and jquery Trevan had written a few years ago.