the developers should not annoy their players with fake checks for your low willpower's sake..
Aren't I a player as well?
I thought it was common knowledge that gamers didn't posses a hive mind . . . but maybe I lost my invite to join the collective. Damnit, this is Chantelle's fifth grade sleepover party all over again. Why am I always excluded??
I also disagree about a single high DC being better, since (for me, personally) it would kill the sense of suspense that the multiple rolls build, which is something I enjoy. Makes my choices have heft. I do feel that multiple convo rolls could be retweaked, however, to encourage player consistency in conversation. For example, if you pass a deception roll--proceeding along that same tangent should make subsequent rolls easier to pass.
I also think this will be less an issue once companions are incorporated better into dialogue, and you're not forced to roll a high-charisma character to pass checks.