If my site is like this: Document library Folder 1 Folder 2 File 1 File 2 I want to require check in and out for File 1 but not the rest of my document library. I know how to require check in and out for the entire library but have yet to find anything that tells me if I can require it for only File 1. I also am aware that the drop down box can permit self checkout but I don't want my users to forget. Doable or not?

Requiring Checkout is a property at the Library level. To enforce it on a specific file and not the rest of the Library about all you could do would be to write a custom event receiver that would intercept the process of downloading a file and require that it be checked out.Paul Stork SharePoint Server MVP