I want to be able to manage checkins/checkouts from Dreamweaver. Is this possible? Dreamweaver CS5 and TFS 2010.
Nope. They don't even have support for TFS in Blend or Expression Web let alone Dreamweaver.
It's not a great answer, but it looks like Dreamweaver CS5 might support Subversion (SVN). You could potentially use SVN Bridge to enable Dreamweaver to talk to TFS.
Essentially SVN Bridge allows Tortoise SVN to talk to TFS. If Dreamweaver can integrate with Tortoise SVN then you may have a winner. Though I have experience using the SVN Bridge, I don't have any exposure to Dreamweaver, so your mileage may vary here.
A couple notes about the SVN Bridge. There haven't been any updates to it since late last year, and we had some issues with the bridge not working in all situations, but that was back in early 2008.
edit: also found this (particularly old, but may still be valid) link just after I posted. This is a different bridge approach but may work as well: MSDN - Using Dreamweaver with TFS