How does one go about selecting several files in a folder or for that matter a entire folder for "upload" with just a simple one click. Right now I need to click "browse" select a file then select "open" then repeat the process for each file. If I am to add 100 pictures does this mean I would have to do this 100 times? I must have missed something in basic training.

I presume you're talking about the Photo Webshare, correct? If you use IE, you get an ActiveX control that allows you to browse your client computer and select entire directories of pictures to upload.

If you reject the ActiveX control or have those disabled in IE, or you're using Firefox, then you only get the single-file upload mechanism.

I should have used another example than photos. I see photos have that option but what of other file types. Specifically I am talking about when I am doing it remotely. I just get the upload box asking for a single file at a time.

The photo software that came from HP surprised me. I thought it would have automatically looked at the pictures in the Pictures share and let me set up albums...

But no, it doesn't. HP is now known for great software but their hardware rocks. I'm sure I can find my own ASP app to run that will do the same trick.

That's a limitation of WHS, I have heard rumors they plan to improve remote multi-file uploads in a future update, but do not know the time line.