carter - I think I know part of what the problem is. You need to find a (preferably established) league with a group of like-minded guys that are for the most part all buddies or at least friendly acquaintances. You definitely need a league with an in-person auction draft. This will feed a lot of your cravings for social baseball-related interaction and pseudo-intellectual behavior. Even if that's the only day of the year they get together, but even better if they have other social events. Maybe a newsletter, but group emails or an active message board will scratch your itch.
Established leagues like this are hard to find. You really have to search and you have to be willing to look at a wide area - maybe even an overnighter for the draft. Maybe be prepared to spend more than you would normally. Classifieds are inundated with online leagues with online drafts with owners that are all strangers to one another. I would search by locations you are willing to go to. Then I would search other fantasy site classifieds. The best resource you might have is just like when you are looking for a job - networking. You never know when your sister-in-law's co-worker's husband is in a league.
I've been in a 20-team mixed league since 1991 that's like what I'm describing and I would just be lost without it. That league is irreplaceable. The friendships, the history, all the inside jokes from the history - we spend as much time laughing on draft day as we do auctioning.
So I don't think it's your league settings, it's your league setting, if you get what I'm saying. Good luck - maybe even plug your location into this thread and strike gold
“Most men lead lives of quiet desperation and go to the grave with the song still in them.” --Henry David Thoreau