I did the hole run without any reload you can chek by yourself. Also I had 24 charisma + friends +proficiency and I failed kind of 20+ times.
Halsin never came to my camp thieflings left w/o party. The gnomes and all thieflings died Damion died. The little gnome girl blowed on me the smoke powder I failed to ascend. And the list is almost endless. But I still did it without a great effort I made a lot of mistakes. I got two huge bugs in the run when I falled down do a geometry bug and when I started to fly in baldur's gate. I needed to load back because I had to. But out of that it was not needed at all.
I actually believe if I whould prepare with companions I would not fail any of those dialog checks. I mostly failed because I had only 6 or something inspiration in the full run.