Team 2 win. With current knowledge, Obito won't be a problem this time.
Kakashi knows he can engage Obito properly without worrying about his phasing by entering the kamui dimension or sending a clone there. This way, Obito can't phase, otherwise he'll be killed. With a clone of either BM Naruto or Kakashi in the kamui dimension, Obito can't do jack, he's better off hiding in Madara's Susanoo.
If Kakashi can kill off Obito, then Madara isn't much problem. BM Naruto and BM Killer Bee will struggle against Madara because of the wood dragon. But Naruto knows he can make BM clones and attack Madara, and even break the wood constructs. So this time it won't be a problem. Continuous tbb and Hirudora will finish Madara.
The knowledge and intel makes a huge difference. They won't experience the same problems this time.