Hussar
Legend
So as you show in your second example, one player is trying to give the other player advantage on the Insight check via working together on the task (or at least tries to). That is reasonable behavior if you're trying to succeed.
Now take it one step further as a player: Before asking the DM to make a check (which is not supported by the rules of this game, but we can ignore that for now), try to remove the uncertainty as to the outcome and/or the meaningful consequence for failure so you don't have to roll at all. The DM can't call for an ability check if there is no uncertainty or meaningful consequence for failure. That may or may not be possible in this specific situation, but that is something the players are aiming for because, again, the d20 is nobody's friend - automatic success is more desirable if success at the least cost is the goal.
But, again, that is the player's goal. The DM is employing the "middle path" approach. In the example I wrote, the DM calls for ability checks because the players have not removed the uncertainty as to the outcome and/or the meaningful consequence of failure.
See, that third paragraph is where I leave the train. You are claiming "middle path" here, but, to me, it's the DM's judgement as to whether or not a skill check should be made. And the reason he's forcing (not granting, because the players don't actually want a skill check) is because the DM isn't convinced that the players have removed uncertainty. The only way the players can remove that uncertainty is to convince the DM.
Thus, we're right back to gaming the DM.
And, frankly, the notion that the players and the DM are playing fundamentally different styles seems like a big warning sign to me as well that will, IME, lead to a lot of frustration at the table. I prefer everyone at the table to be singing from the same hymn book and all playing the same style.