redrick
First Post
Any DM that's run with a six player group (or more,) starts to realize that with everybody rolling the same check groups of adventurers succeed at almost everything. If they don't want to do the three pillars thing and are basically just trying to get into the next fight maybe that works for them, but for actually putting some emphasis on the exploration and social interaction parts of the game, a DM will usually only let one player make a roll for a particular check.
As such you want the guy that knows what he's doing to track the dangerous beasty back to its lair or try to get the diplomat to add a corrupt little side clause to the legislation that's being voted on today. As a Jack of all Trades you become the natural fit for whatever skills don't happen to have a more experienced person around for.
D&D gets run a little differently by every DM that puts their hand to it, but I don't think I could stand a group that had everyone hurling their dice on every task, except maybe some custom scenario where we're actually adding them all up for the unusual scenario, and didn't think the help action adequately covered what was going on.
Personally, I like to run this as: only so many characters may attempt a certain thing at a certain time. So, if 5 PCs are trying to track an NPC back to his or her lair, that's 5 PCs scuffing up the tracks.
When one character attempts something, and then fails, and then another player says, "oh, well, can my character make an insight check?" I advance the timeline first, or nix the check, as appropriate. Characters can't round robin every check until somebody succeeds. At best, if more than one character attempts something at the same time (without a good reason why 3 characters are better than one, like a strength check hauling on a series of ropes), it's all just "aid another", which grants advantage. Advantage doesn't stack.
That way, it's on the players to sort of "prioritize" skilled characters over other characters, knowing that if Billy the Absent-Minded Wizard tries to track the beast, Steve the Ranger might not be able to. On the other hand, if Steve the Ranger is otherwise occupied, and Billy wants to give it a shot, more power to him.
(We also use a loose sense of "turns" in most situations, so I'll frequently go around the table and ask everybody what their character is doing before calling for rolls, checks, etc.)
As to the OP, yeah, your DM's house rules sound whack. Maybe he is also new to the system? Don't be afraid to find a new game, but, if it's just another guy (like you) still learning the ropes of a new game, cut him some slack. Focus less on him "shafting your character" and just on having a good game, overall. If after a few sessions, your character is clearly not able to contribute, bring it up again, and, if he still isn't interesting in reconsidering his approach, walk away. But, that being said, as a first-time player, be prepared for your expectations to be way off. You came into this with a lot of analysis and preparation, and, without the context of actually playing the game, that preparation is likely to have steered you a little off-course as to what to actually expect from a 5e game.