Unfortunately "people will do what is best for others at their own detriment" usually doesn't pan out too well.
Yeah maybe I'm being naïve. Don't know. It just doesn't seem like the largest miners need to have potentially 150 shares in the share chain at a given time, when they could have 15 shares worth 10x as much instead. There isn't a real 'detriment' here as you'll still earn the same amount of income on average.
Also a big miner shouldn't view p2pool share difficulty as "very high".
I don't have the math to come up with a confidence interval on the # of shares someone will have in the share chain for a given hash power off the top of my head. However, for sake of example, lets say the huge miner with 150 share on average has high confidence to be in the 130-170 range. Likewise, if his diff target was ten times higher, he'd be 13-17 with 15 on average. If each share of normal difficulty paid out .01 BTC for simplicity (.1 BTC for the 10x higher target shares), then his income averages 150 * .01 or 15 * .1, 1.5 BTC either way. The question is if the steps within this range are steps of .01 BTC each or .1 BTC each.
When I used to run sha256 alt coin p2pool nodes and would mine on them with my S1, I'd set /DIFF as high as I could to not shut out GPU miners. I know, few people likely do that in the p2pool BTC world, which is why it makes more sense for p2pool to automatically scale the vardiff beyond just minimizing network traffic and be smart regarding the fact the sharechain is a fixed size.
I guess my point is the # of shares in the sharechain is a resource that needs to be managed as intelligently as possible for the health of the network. For each big miner with 100+ shares in the chain at any one time, there will be far more miners struggling to keep just 1 share active at all times.
Edit: On a sidenote I sent an email to windpath with various old links and github patches in case he wants to apply some nice front end improvements from last year. It seems p2pool-node-status went quiet before they moved from -devel to the normal branch, and the alt coins that also used the interface all faded away. So the cool improvements to show things like estimated time per share and miner-specific difficulty targets have been forgotten to the sands of time.