To make a long story short I was trying to get RSS campaign set up for my Mail Chimp Account and I couldn't get the RSS to filter by category. So I tried a different install of WordPress that had the All in One SEO and it worked perfect.
Digging deeper into my investigation I realized that it was the
/category/ That WordPress was looking for a category feed.
If I would try to get the feed for this specific category it would always re-direct to the page.
eg. >> http://32spokes.com/free-tips/feed always re-directed to
But the site wide feed always worked properly as an RSS feed.
I then removed this setting:
Strip the category base (usually /category/) from the category URL.
The Category Feed generated perfectly.
So for now and the foreseeable future I guess I will have to keep the category in my permalink structure. (Not really a bad thing, Just something a little buggy)