After considering the feedback from players and the comments in the previous post here are a few lessons that I will try to implement:
1) More treasure. I made a post HERE that I knew I was being too stingy with the loot. This may have fed unwittingly into the issue where the party was unwilling to hire retainers or spend money to gather information.
2) Have explicit out of game discussions about philosophy and design instead of have these things discovered in game. I'm still not too sure about this one. I learned how to play B/X D&D without such hand holding. In fact, some of the most memorable sessions were the ones where lessons were learned. But if it is what it takes to get players to learn and appreciate B/X then okay. [EDIT: Not that this is tough to get anyway with this blog which is linked on the campaign website which also contains a bunch of stuff]
3) One thing I have been considering is inserting an NPC party that can play the role of competition and foil. The characters can then see the NPCs hire retainers, buy drinks for sailors, etc. I am still not 100% sure on this one. Does it take away from the party's sense of accomplishment?
Things I am not going to do:
1) Reduce the danger level. The encounters in the Northern Marches have been by-the-book in terms of difficulty and I even took it easy on the party tactically a couple of times.
2) Change my underlying philosophy about B/X and my "gameist" preferences.
Are there any other suggestions? Any comments?