When I say more sadistic with the quests, I meant make them more challenging/harrowing to players. This may have been a little creative interpretation on my part, but I'll see if we can grant that wish that it's entirely possible nobody made and turn the challenge up to 11 for some of these.
I'll see what can be done about providing more detailed directions in quest assignments. Certainly if a player is asked to kill the chieftan in a damnable orc cave, they should have directions from the nearest landmark.
Group quests are tricky. It shouldn't be possible for one person to fulfill the entire group's obligation while the rest play cards in Candlekeep, but it definitely makes sense not to force a party of six line up to talk to Matty and Malcom Burrows in order to find their six lost keys. In implementing future quests, we may advance the quest state for all party members in the current area who were at the previous state. Perhaps we would only let the party leader decide how to turn in the quest, since that provides some options. (I realize Party Leader is an often used as an OOC mechanic, but perhaps it would be wise to make that choice IC!)
With regards to eviler quests (towards players, not Evil), Hoihe's post seems like an invitation to send folks to
I like the idea of sending higher-level players to higher-level areas instead. Fine, so Stewart Hipp prooobably doesn't have a package that needs to be delivered to Avernus, but the Torregir Mining Company might have heard of people returning with darksteel from the Shadow Realm...
The possibility of a quest-like activity to "unlock" a dungeon once per reset also feels kind of appealing. Maybe the first person through the Minotaur ruins needs to find a key to the gate, or pick the lock with a high DC. (Of course, this brings about the concern of getting out
if you resume your dungeon run after it's interrupted by a reset, but surely you get the idea.) It's definitely a good thought to bring "dungeoneering" more prominently into the server.