Generally when I read people's posts I am watching for a few things:
1) How do they use the system? When I first created Obsidian I expected people to use it as I had wrote it, but more and more posts have convinced me that the majority of people use it as a framework to implement their own ideas. That's just fine by me, and that drives a lot of the work I do on it now.
When I consider new versions now, my main focus is maintaining that solid baseline while adding features that create value. Obsidian's greatest advantage is flexibility, you can add a +2 here or there and still feel like the system works.
2) How often are people succeeding at Obsidian? Basically...is the math working out to my expectations, and that has a lot to do with number 1. I mentioned in my previous notes that my party was succeeding with more regularity that I had anticipated, but that seems to be the way we play with the system. If others are doing the same, then it may call for a change in the baseline assumptions.
3) Do players enjoy the system...or even skill challenges in general? The whole concept of using set mechanics to determine what used to be wholly just roleplay talk is still a new thing for
4e...and ultimately the question becomes is it a good thing?
One thing I have learned from my experience playing and running Obsidian challenges is that I like my skill challenges to be infrequent and a big deal. I don't use them for regular negotiations or persuasion, I don't use them for general moving around the world. I only use them for a big chase, a very important negotiation, or a critical piece of information.
I hope that answers some of your questions about my answers to your answers
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