Could you try using Failed Request Tracing (aka FREB) to get more data? You can enable it for "default web site" running the following commands:
%windir%\system32\inetsrv\appcmd configure trace "Default Web Site/" /enablesite
%windir%\system32\inetsrv\appcmd configure trace "Default Web Site/" /enable /statusCodes:"200-600"
After that you should request the page normally, and you will find the XML log files at "c:\inetpub\logs\FailedReqLogFiles\<SITE>". Open the XML files and switch to "Compact View", you will find there the details of Static compression, search for "STATIC_COMPRESSION", and you will find more info, for example, in my case the files were not hit frequently enough to trigger the compression (If I remember at least correctly 2 times in 2 seconds).
| STATIC_COMPRESSION_NOT_SUCCESS |
Reason="NOT_FREQUENTLY_HIT" |