We use Visual Source Safe. Is there a way to have the all-files-checked-out-to-me report display on the Start Page in Visual Studio? So that when I opened VS, I'd see a report of everything I have checked out from VSS, categorized by project.
I don't think there is a way to customize the Start Page. You should be able to see all your checked-out (and modified) files in the Pending Changes window. Beyond that you'd probably have to customize VS with an Addin or Package.
Visual Studio 2010 allows customization of the start page, altough I don't know if this could solve your problem.
This is probably a more complicated approach than you're interested in, but since the start page can show RSS feeds, you could write a web app that would query VSS via the COM interface, list your checkouts, and publish that as a feed.
If you're not looking to roll your own, I did a quick search and came across VssRssSvc, an application that generates RSS feeds from a VSS database. It includes source, so you'd be pretty close to getting what you're after with a little bit of work.
If you decide to build it, let me know. :)