semanage not changing file context

Could it be the fact that "latest" is a softlink and semanage does not like softlink in the full path?

Yes, thats exactly why.

From man 3 matchpathcon

NAME
       matchpathcon, matchpathcon_index - get the default SELinux security context for the specified path from the file contexts configuration
...
DESCRIPTION
...
       matchpathcon() matches the specified pathname, after transformation via realpath(3)...

Just to clarify, realpath(3) expands all symbolic links in the path to attempt to define the absolute canonical path to the file.

You could probably specify the PCRE as /WMSData1/tomcat/[^/]+/logs(/.*)? instead to avoid the problem in a manner that means you dont have to continually add new file contexts.

Path mismatch? Symlink?

/WMSData1/tomcat/latest/logs

vs.

/WMSData1/tomcat/apache-tomcat-8.5.37/logs

This:

/WMSData1/tomcat/latest/logs(/.*)?

is a regular expression, that does not match the apache-tomcat-8.5.37 path.

For more details on regex see: https://regex101.com/