Had another look at your question, and I think may have overlooked something. If you care about actual contents of the files being checked in, then the client side Visual Studio add-in may be the option for you, as then you will have an easy access to actual files that were checked in. CommitCheckinEventArgs passed to CommitCheckin event will have all information required.
The VersionControlServer events are not documented extensively in MSDN, but there are lots of basic VersionControlServer examples (see the following Buck Hodges post, for example), and once you have VersionControlServer instance usual event handling techniques apply.
Regards, Eugene
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