Mobs on the other side of the painting have to run all the way to the back of the wing and use the portal to get to the entrance the same as players. This applies to any wing not just South.
Just make sure you can see the mob you're lulling either with bind sight or through the wall so if it crit resists you can camp immediately. Give a heads up to anyone camping entrance as well on the slim chance the mobs make it to entrance.
For transferring I usually drop transferred, OT is huge and also has a very long ocean edge. I never had anything stolen but if you want to transfer something you're not comfortable drop transferring then yeah ask a player.
If I had to make another lvl 5 key mule I'd go with a Dark Elf Enchanter because they have invis and can roam freely in the outpost. When I made the halfling rogue I didn't know you had to be level 5 to zone into OT until I tried to zone in and was rejected.
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