@blowdart: What is interesting is the date/time of the truecrypt file on the local skydrive directory is the same date/time as when the file was originally created, even though the contents within the file have been updated almost daily since the original creation. This completely/partially may be why skydrive doesn't think it needs to be synced.
Ah yes! You need to tell trucrypt to update the last written attribute
Settings > Preferences > Windows and uncheck "Preserve modification timestamp of file containers"