First of all, I'm honored someone's work has been inspired by my own
Let me start of by saying: I'm extremely impressed at first glance.
I have been thinking about various tweaks to Obsidian to incorporate some of the things your system has done naturally. The highlights:
1) DM vs Player skill challenges: The fact that you let the players "fight" the DM by escalating the DC is a simple but powerful way to go.
2) Adjustments for secondary skills: Your -1 SP idea is a great way to handle secondary skills.
3) Adjustments to higher skill checks. I really like how you account for higher skill checks with more successes. In a way it rewards better skill...but it also contains that power with a large gradient of successes.
4) Variable challenge: I like how your failure system can make different parts of the system come back to bite the players. Like the tribal one, the party is doing all sorts of religious negotiation and suddenly a slip in the basic lingo sets you all the way back.
5) Variable complications: They set to really differentiate the challenges nicely.
6) Complexity in the right places. Your system is definitely more complex than mine, but I think you put it mostly on the dms shoulders, and allow the players to interact without a whole lot of mechanical knowledge.
Now my critiques:
1) Insight system seems like a needless addition: Currently I feel the insight area is a way to tell the players things most DMs would just tell them anyway, and it feels like rolling for rolling sake. With the amount of complexity you are going for, I think you can clean up your system a bit by taking this aspect out.
2) No partial successes: Probably the biggest praise I've gotten from my system is the addition of partial successes. I see no reason your system can't incorporate them and I highly encourage it.
3) Need gameplay examples: I'll post my notes below, but right now for me some of the language is pretty confusing. Even one example that details all of the rolls and decisions of a skill challenge goes a long way to clarifying the bits that language sometimes leaves unclear.
My confusions:
1) Conflicts handled together or all at once? I believe the answer is every conflict is handled in each segment, but its confusing because you start out talking about how each conflict is handled in order.
2) How many checks does each character roll? I gathered that its 3 checks per conflict per segment....regardless of the number of players? So if I have 4 conflicts that's 12 checks...so if I have 5 players....an average of 2 checks a piece with 2 players making 3. Is that correct?
3) The -5 rule. So if a character makes 2 checks in the same challenge, he gets a -5 to the second. If he uses the same skill, is that a -10? If two characters both use the same skill in a conflict, is the second one at a -5? If a character uses the same skill in two different conflicts, is he at a -5 to the second conflict?
4) Spend a surge to stop failure. What does "one last check to stop the failure" mean? Does that mean I'm trying to boost the failure DC high enough to stop the failure? Or perhaps that I'm opposing the role?
5) Should failure checks be rolled in order? Since I can only get one failure per segment, should I roll failure on conflict 1 then conflict 2, etc...or can I pick the order?
6) Complication - So any time a failure is received someone must immediately spend 2 surges or the challenge is over right? Does it have to be someone participating in that conflict? Also as a note, not a big fan of always using surges, I could see times when surges might not make sense.
7) Individual - Does every player roll a check on an individual challenge every segment or can only 3 do so since its normally 3 checks. Also for failure rolls, so I roll once but apply the failure to every players DC who is low enough correct?
The math: Ultimately I love the form of your system, but its got to past the ultimate test....how does the math pan out. However, I'm so interested in your mechanics that if you'll correct my confusions I would like to do so math modeling and see how it looks.