Does this happen only after reboot? Looks like mod_cfml is having a long time to verify all the contexts, but I’m not really sure.
After reboot Lucee/Tomcat may be reinspecting the web contexts of your 110 websites. Also, your templates will be recompiled on each first request (by default). If you have a good amount of websites that also have a good amount of well known/popular URLs (visitors and bots), templates may be getting requested again and again during all that web context and template inspection/compilation occurs.
Usually these requests would just time out by Tomcat, but if you have tweaked the default IIS or tomcat settings, it’s possible that IIS 500errors will be generated before that happens.
To rule that out, I’d try rebooting the server with port 80/443 closed/blocked per firewall in such a manner that only you can retrieve the URLs locally. Then monitor your catalina.out and wait until Tomcat finishes every web context scan and Tomcat gets fully available. Then try opening URLs locally over port 80/443 and check if the issue persists.
The steps above are only to identify the issue. If identified you can take further steps to avoid the 500errors.