Yes and Yes. Mapping can work in 3 layers, and events can pretty much do anything you want them too. If there isn't an option for something, you can use your own code to make it happen.
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I had a couple questions about Essentials from the technical standpoint.
1) Does it support Multi layer mapping? This might break some things.
2) Are character effect events supported? Ie healing the party.
I figure I'd ask these. Not to important just it might break some things.
Yes and Yes. Mapping can work in 3 layers, and events can pretty much do anything you want them too. If there isn't an option for something, you can use your own code to make it happen.
1) I can confirm that 3 layer mapping is supported. All mapping is basically done through the RPGMaker XP interface and then there's some script that debugs them so the transitions are seamless. All events are also done through the event editor, which brings me to your next question
2) Poccil's I'm pretty sure has a script to make healing happen in Pokemon Centers and through your Mom. You'd just reuse that script on a different NPC/switch to make it happen. Scripting your own character effect events probably doesn't work like you think, because Poccil's doesn't use RPG Maker's "Actors" interface, so I don't think there really are characters to have effects on. But most conceivable things should be possible and present in the scripts available.