With Pain on her side, Obito will surely not underestimate them like he did with Konan. With Pain on her side, Konan would have to be cautious when using her trap in order not to take them with the attack. Pain has a flying summon true, but the time to summon it, stay on it, and go out of the range is slower than Obito simply teleporting himself out of the way, so if even Obito couldn't, Pain sure as hell won't as well. Now some may say Pain will start flying under Konan's order, but you must notice that Pain only has one bird summon, so all the Paths will surely not stay on that bird alone, and even if they did, Obito will be stupid not to suspect something will be coming from underground if he sees all the Paths holding their own in the sky instead of fighting