Once I enable the require SSL, the website changes to a ridiculous font. This is the same cert as our existing web server that I exported/imported without and issue. Note the screens - the first one is with SSL requirement on.
Without the SSL requirement.
Could you change you log level WARN to DEBUG in \Inetpub\Solarwinds\web.config, reload a few pages with the problem, and send your OrionWeb.log file by private message?
I would love to if I had a web.config file. Is this because the server is the additional web server?
No web.config file? That's a real problem. Are you sure you're looking in the proper directory for your website? If so, it's time to look at the ConfigurationWizard.log file (it's in Program Files\Solarwinds\Orion).