Speaking from my own experience, I developed several packages with VS 2005-2013 support. I use Wix generating .msi that copies files and writes to HKLM\Software\Microsoft\VisualStudio\x.0. Supporting only VS 2005/2008 from an .msi should be even more simple.
Visual Studio gallery doesn't extract anything from msi (you can even just post a link to your site). I don't have links to good samples, but basically you need to add info about your package to HKLM\Software\Microsoft\VisualStudio\9.0\Packages plus Menus and ToolWindows.