Question: To create skins do I only need to build in SkinStudio or is there a prefered way to test skins as you build them?

A Windowblind is built in Skin studio (SKS) The first thing you should make is the startmenu. Complete each section in SKS. You can open SKS and load the Diamond skin into it. This skin can be used as your template. Each section needs to be skinned. Make new images for for each area in each section that is showing images already there by making your own and replacing what is there with your images.

This all sounds easy but a lot of time will be needed to do it correctly.

Here is a link that will let you make a complete WB. There are no shortcuts when making a WB. Take your time.

https://dl.dropboxusercontent.com/u/3083208/Files/SkinStudio%20Tutorial.zip

In each are of SkinStudio there is a "Test skin " link, but it's not very useful IMO. Easiest way is to apply your skin often as you work on it and check the results. 

Thanks for the help! I had another question, I'm using windows 8.1 (I know, bad choice) Do I need Start8 in order for WB to skin the start button? Right now I apply a skin with a unique start button but only see the default white windows button.

Yes.

There are a lot of start buttons available and you could also make you own.

https://www.wincustomize.com/explore/start8_buttons

Thanks, that did it.