Manga intel? Gai basicly knows 2 out of 3 fighters' whole moveset, he pretty much knows Tsunade and Sakura being her student. Same can be said for the other team though due to his pupils being there.
He would take 1st scenario since the other team would burnt to crisp by Asakujaku and smashed by Hirudora (maybe he won't have to go that high up) and none of the team's taijutsu skills are near his level, he can counter it very well.
Second can be won by team if Sakura's healing abilities and Katsuya make them survive somehow until Gai runs out; still slim though.