I finally figured it out for anyone wondering it was related to this question Tomcat Service gets installed with "Local Service" account
Long story short sometime after Tomcat 9.0.30 there was a change to Commons Daemon
Commons Daemon 1.2.0 onwards will default to running the service as the LocalService user rather than LocalSystem. That will break a default Tomcat install via the installer since LocalService won't have the necessary rights to the work dir for JSPs to work (and there may be a bunch of other issues too).
I was able to adjust my script to update the service before starting and everything is working again.
PowerShell
cmd.exe /c "tomcat9 //US//Tomcat9 --ServiceUser=LocalSystem"