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Quickly make an army of 7 Arachnids (might be worth tossing starting creatures, imps I think? down the hatch at the Dungeon Heart, because arachnids are better), they are the best creature for this kind of mission which rewards being highly offensive. Micro them to keep them alive (pull back weak ones, send forward strong ones) and take advantage of demon regeneration. Be aggressive on the overworld. Use Demon Portal to move your army back to the base and to defend Crowley when you absolutely must, and note Demon Portal can be cast at an Island of Evilness near the flag.
Order your zombies to follow Crowley, they will escort him forward, until the heroes/towers kill the zombies, it's okay. It'll take the heroes a while to push Crowley back and the zombies cost nothing to throw away.
Use your evilness to invest in more Arachnids and maybe some Succubi. Spells are also very, helpful if you are "gud" enough to use them. I hotkey Demon Portal, Mana Shield and Meteor Swarm to " , . / " so I can quickly spam them on a battle.
Once your arachnids have mostly wiped out everything on the overworld then take your big powerful army and escort Crowley forward.
They have very little downtime but you can quickly end up in a fail state if you run out of mana, just make sure to have one or two producing some constantly and you can pretty much rush most of the map.
You can send them back to defend if not getting traps and just send them back out afterwards. They are alot squishier than something like horde, but their damage is great.
The first half of this mission should be securing your side of the overworld (from the southwest entrance to the cliff where the catapult ambush is), doing researches to expand your minions and dungeon, and securing your dungeon. I know it is a tedious task since you have to monitor Crowley as well, but it should be easy.
Once all the areas on your side of the map is conquered, proceeded to Yaina's side of the map by either the path on the far right or through the defenses in front of the northwest dungeon entrance. Clear the catapults and surrounding strategic 'Good' areas before pushing Crowley to the front gate of Dollaran
After this, it should be routine: push into Dollaran and kick Yaina Overproud's rear
Get things of his back
get your first island of evil
consolidate your hero lanes into one
build an army and clear the map like any other mission
It's less urgent than it's pretending to be.