Hi Jarret,
I'm managing a dozen of .NET developers on several ASP.NET projects (with SVN as source control), and I confirm it's a real pain to maintain web.config between them !
Itchi : each developer may want to have his own connection string, informations to get automatic connected to an application, etc.
I solved this by using NANT (http://nant.sourceforge.net) in all our .NET projects, basically :
1) genuine web.config is moved as a template in a subfolder
2) Hard coded values must be remplaced with ${your_property} properties
3) genuine web.config is marked as ignored in SVN
4) each developer create his property file (whose name must include at least the current Windows username), with personal properties
5) a NANT's build file must be created to load the current Windows username property file, then copy the templated web.config to the genuine place (with extended properties)
6) NANT is triggered during the Visual Studio's pre-build, to execute the build file
That's all folk, now each developer can manage it's own property file stored in SVN, independently of the machine it's connected (as long as the Windows username is the same of course)
You can extend this behaviour with the machine name, the current configuration, etc.
Note : altought Microsoft introduced web.config transforms in Visual Studio 2010, there is still not a solution for per developer web.config ?