As it stands your team is likely overkill for cloudy weather. In neutral weather you'll probably fall a little short. I would also recomment becoming "friends" with any people willing to short trainer raids since we'll get damage bonuses as the friendship progresses. But here is a video of a regice quad in cloudy weather.
1 trainer 3xLv 40 machamp and 3xlv30ish (max-revives)
1 trainer 1Lv 40 moltres and 5 lv 40 machamp and gets dodge glitched (max revives)
1 trainer uses second team of fire types (moltres, entei, etc)
1 trainer takes 50s to rejoin with second team
still wins with over 30s to go (granted it's the easiest moveset)
https://youtu.be/U-PBugpr-r4