I ran the game at Camp Nerdly 3 at the end of May 2009, and had a great time; it was a very satisfying run. But I was sensitized to pay attention to problematic aspects of running the game. And a conversation I had with independent insurgent and indie game designer Rob Bohl helped me identify one.
In Trail of Cthulhu, when you have a "contest" between two characters -- one is chasing the other, or some such -- you roll until someone fails, spending your precious skill pool points on each roll. This has a number of unhappy effects, chief among which is that it makes contests largely an exercise in die-rolling and point-spending, with the edge going to the character who can outspend the other.
Fixing the Contest
It might be more fun if there were some "tactical" decision-making going on. The idea I had on the drive home from Nerdly was this: you spend for an automatic success, but the amount you have to spend goes up each round until you "reset" by rolling instead of spending.
So, for example, if you're chasing me, you spend from your Athletics and I spend from my Athletics and/or Fleeing. On the first round, you spend 1 for an automatic success and so do I. On the next round, you roll and I spend 2 for an automatic success. On the third round, we both spend for automatic successes, but I have to spend 3 and you spend only 1, because you "reset" in the last round.
This strikes me as setting up an interesting choice for players each round. Now, I think that there should be a system for setting the difficulty of the roll based on the differential between the two pools. I think for every 3 points you are lower or higher than the opponent, your target number of 4 goes up or down by one, rounded down. So if your Athletics is 8 and my Fleeing is 12, my skill roll is 3 or higher and yours is 5 or better.
This means that if the differential is 10 or more, the lower value automatically fails on the roll and the higher value automatically wins -- no rolling necessary. Or should there be a 6 always succeeds, 1 always fails rule? Probably yes.
You could use a similar system in combat, where a hit always takes an opponent out unless the victim succeeds on a roll of Health versus the damage.
I will try this at Dexcon and see if it works.