My server admin once tried combatting the veterans lack of challenege 'end game' by restarting the server and telling us he was going to crank up the difficulty past what he usually set his little vanilla server to after a point to better scale with our skills and resources. This was great for us, for a while, but it also discouraged server growth. We had a server with all these slots open that had been getting players around the clock, but this increase in difficulty for new players meant unless we spoiled their 'immersion' by giving them materials people usually got flattenned. We more often than not just got people coming in, getting freebies and then playing a for a short time and leaving or chain dying abit and going someplace else.
I recalled thinking the auto scaling for skyrim was weird sometimes back when I played that before modding it to get the game to feel just right. I keep thinking we need something like that. But honestly, how to do it, I'm not sure. =/ I don't think bethedesa quite got it right either.