Embroidery

Not sure what the most popular software is, I think it has do to more with what software is best for the type of machines you have. I use DesignShop and it can save in pretty much every embroidery format. Almost every machine brand has a different file format.

With vectors now it makes digitizing easier. Before you used to have to redraw the whole logo, but now days you can open a vector file and convert most of the file easily. You might have to adjust stitch directions some what, but it's an easy fix. Certain elements might need to be redrawn, or often stock lettering inserted. Lettering that has been made for embroidery comes out much better the just converting from vector or using system fonts.

Zilch, I have seen lots of the stuff you have vectorized, and adding embroidery digitizing to your list of skills would be easy for you. Honestly, the hardest part is just learning how the different material/fabrics you will embroider on works. Hopefully you will have access to a machine to run samples on and test your designs. Once you know how the fabric reacts, it's really easy. That and also getting used to the way the design looks on the screen. What I mean by that is, sometimes on the screen you might have a column or some lettering that looks way too wide or fat on the screen, but when it sews out it looks fine because of the amount thread that sinks into the fabric.