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What I did was 100% the Underdark right up until using the elevator then I moved to the Mountain pass, did the Creche for Lae'Zel and then moved on to Elminster. Gale only requested two items in my playthrough and after that the game said giving him items to consume wasn't working anymore and he never asked for 30+ hours for another item or got any negative traits for waiting around after that.
If you want to go back to the earlier areas and clear both parts for your companion quests there's one part in Act 2 that will be the true no point of return. It's the Shar Temple.
I think the safest option is to do all the content in both the Underdark and Mountain Pass up until you reach both points of no return(Elevator in the Underdark / Shadowcursed Lands just after Mount Pass) and then when you've done all quests move onto the next area from either the Underdark elevator or Mountain Pass but don't progress Act 2 by completing the Shar Temple
There are a couple of quests between entering act 2 and finishing Moonrise tower.
You could never enter Moonrise via the Underdark, that is misinformation. The Underdark exit into the shadowlands is near the other one, but the Underdark has more area than the creche. And both are on the other side of the shadowlands map as Moonrise.