At this point I'm completely stumped and thinking that I should turn the entire server off and on again. I persist and continue to screw around with things i don't even understand, haphazardly adding stack overflow fixes in here and there since I was at my wits end. I eventually try cloning it again and, god knows why, it worked.
If I had to take a guess at why this happened, I'd IMAGINE that it's because some of the bootstrap functionality is simply linked to in my application.html.erb file. And since this server has no SSL cert at this moment in time, I can see them rejecting it (At least temporarily) until some merciful soul in power somewhere took a look at this logsite and said "Ah he doesn't look like trouble, leave him off...".
In any case, this took up so much of my free time that I figured I'd get a blog post out of it.
Lesson learned: Turning it off and on again once is sometimes not enough.