Ok first off, I have to say I hate Visual Source Safe (VSS)!
Actually hate isn't right I despise it, I loath it, it is the worst source control software I have ever used! Well I feel better getting that of my chest.
Anyway back to the reason for this post. If you need to recursively add files and folders to VSS you simple drag the folder from Windows Explorer and drop in in the correct location in your VSS project.
You might think there is a menu option to do this but there isn't. You may also think well if I hit insert I will be asked to recursively add, and you would be wrong. Then you may think Let me look in the doc, maybe it is a command line option, good luck.
Anyway I hope I am not the only id10t to forget how to do this and had to go hunting for it.