So my group got to playtest the Obsidian system, and my DM decided to put it through the ringer. We had 5 skill challenges tonight, all of different shapes and sizes.
The first one was a Mental Challenge were my wizard and our party's warlock did some research on the big bad guy we are looking for. We rolled very well and got a victory, finding out lots of information about him.
The second was a social challenge. The party's cleric and rogue were looking for a stolen object, and found a disreputable looking guy they thought might have a clue. They failed the challenge, and so the guy led them alright, towards a trap. The cleric used his insight and noticed something was up, so the two entered a mental challenge, using insight and perception to watch for when the guy might turn on them. They got a partial success, so they were still led into the trap but were able to prepare before it was sprung. They finished with a physical challenge to run from the thieves. They got a total success using stealth, endurance, and athletics and were able to escape.
Later we all got together again and went into a mental/social challenge to find out where the big bad guy's hideout was in the bad part of town was. It came down to the wire, a few action points were used and it was down to the last roll. We had a partial victory with 7 successes, and the warlock missed. He rerolled with an action point but still failed, so we were able to find the hideout and get there, but the Big Bad knew we were coming.
All in all I was extremely happy with how things worked out. People started out in the "mechanical" mindframe they had gotten used to, but as things went on people started role-playing more and just going with it. People were using the primary skills a lot, even when they weren't their best skills. The cleric even got a critical success on a nature check, and its one of his worst skills!
Also, the three phases helped to move the story along. In the first phase I was working with one party member, by the third we all had moved around and were working with different group members and using different skills. It also allowed the DM to disseminate information in pieces as we gained successes.
The one thing I was worried about was the DC. As a player, 18 felt high to me. I was heartbroken when my buddies would get a 17 and found out they failed. But looking at the results everything came out as expected, we had 1 failure, 2 partials, and 2 totals....right about what I expected.
Right now I couldn't be happier.