Or is this impossible? can anyone from ESRI confirm if this is doable?
Unfortunately, you can't, as the underlying web server requires case sensitivity. There are a few good resources as to why case sensitivity is important:
How to config Tomcat for case insensitive URL? - Stack Overflow
URLs in general are case-sensitive (with the exception of machine names). There may be URLs, or parts of URLs, where case doesn't matter, but identifying these may not be easy. Users should always consider that URLs are case-sensitive.
Apache Tomcat Configuration Reference (6.0.53) - The Context Container
caseSensitive | Deprecated. This option is removed in Tomcat 7 onwards where the default of If the value of this flag is NOTE: This flag MUST NOT be set to false on the Windows platform (or any other OS which does not have a case sensitive filesystem), as it will disable case sensitivity checks, allowing JSP source code disclosure, among other security problems. |