Going into a partnership with another website such as www.rpgoutfitter.com?
I love the guild web site system you built, and all the integration it has. I do wish the character tracking information was a little more feature rich like the RPGOutfitter website, and know that you tend to build the functionality first and make it pretty later.
So I was thinking, would it be just as easy to tap into another websystem out there (such as the free one RPGOutfitter provides) to collect character and overall guild information? Yes I know we can link their pages through our guild site, but that isn't true integration. The concept of leveraging the character/guild information tracking over to a third party would in theory free you up to focus on other aspects of the guild website.
Don't get me wrong, I love the automated character uploading feature you have and that it does update my toon information, but my personal opinion is that the gear and skills of my toon are organized and graphically presented just a tad better through the RPGOutfitter system.

Again just a thought of a way to add even more enhancement while at the same time removing some workload from you in the end.