While it can be annoying to lose a roll I would like to stress that more often than not skill checks aren't exactly barring people out of vital stuff. Winning one frequently just means receiving a small hint about something.
In other cases (i.e. the scene with the viper druid and the thielf child) the consequences are a bit more dire but it's also clear that the "bad" outcome is supposed to be the default one and managing to save the situation is supposed to be a fringe scenario.
Yeah one of the best aspects of the game is that you will not loose out of content if you fail a speech check. If anything, you loose out of content by hitting the check. I have yet to find a situation that cannot be solved several other ways if I fail a check. That being said, I agree you should not have to roll several times to achieve one thing. It makes me think of a new DM who forces the rogue to roll a stealth check for every guard he sneaks past on his way to X location.
