Well lots of issues here...
I can't understand how running slim.exe then opening a web page is
complicated?
I have SlimServer bookmarked in my web browser, and I have a shortcut to
slim.exe in my startup folder.

Secondly, the plugin is unlikely to ever easily work when SlimServer
runs as a service. 
It's a Windows issue that it doesn't appear to be possible to get
around.

Now the good news;
There is a way to still use the plugin although if you have issues with
DOS you're not going to like this either.
You can disable the 'direct update' plugin mode, then all updates are
stored in a log file. 
They can then be independently applied to iTunes manually or by a
scheduled process. 
The instructions are in the readme file, but you will need to install
ActiveState Perl and run/schedule DOS commands. 

James
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