As I suspected Upholstering is hard.  Seems likely that this is why it's costs hundreds of dollars to have someone do it right.

I bought this chair for $20 off of Kijiji. (steal!)  I kind of liked it as is but the chair was covered in vinyl and a bit grungy so I thought it might be an easy first attempt and upholstering.

Before:

I had to carefully remove the upholstery tacks so I could reuse them.  I pulled off the vinyl removing as many of the staples as possible.

Then I lay batting then hot glued the edges and trimmed.

After:

The fabric wasn't my first choice and I stood in the fabric store for about 45 minutes pondering.  I originally wanted blue velvet but the only had this weird crushed velvet which I thought was potentially far to pimp-like.  I settled on this tweedy wool instead.

Cutting the Fabric to exactly the right size was a bit tricky.  As was getting the fabric tight enough to not show ripples.  I did my best.  I reused the upholstery tacks to finish it off.

I'm 80% pleased with the final product.  Maybe, just maybe I'll try it again someday.