When using the Apache tool, rotatelogs.exe, you can see (using the task manager) multiple instances of rotatelogs.exe. Even when using it on just 1 web site!
To make this issue even more disastrous when restarting the Apache (httpd.exe), not all instances of rotatelog.exe are released.
Doing some research on the web it looks like this issue has been going on since years (Apache 1.3, 2.0 and now 2.2....).
Note: I've verified this issue with both Apache 2.0.55 and 2.2.0

Conclusion: It is unusable and dangerous (it will eat up all your memory/file handlers ...etc...).
You can not even use rotatelogs.exe on 4+ sites, Apache will lockup when starting (tested on Apache 2.2.0).

This is a "bummer" since the rotatelogs.exe enabled us (i.e. Windows System Administrator) to nicely name the logs like IIS. This worked very well for my existing custom Awstats application that relies on the logs being named ex%y%m%d.log.
Update: I easily updated by custom awstats application to work using: Apache Better Log Rotation mod_log_rotate

My recommendation at this point is to use mod_log_rotate see:
Apache Better Log Rotation mod_log_rotate

Note: cronolog.exe behaves exactly like rotatelogs.exe (so this is most likely a bug with Apache_Win32).
For search: apache rotatelogs exe bug