Well, the real thing you have to consider is this: When running from an enemy, how can you expect to get away from them by going through an AT, an object/area that is completely OOC? If there are spawns that are left at the AT, that's different, however... Running from a spawn by heading through an AT is against server rules, because, as tends to happen, people try transitioning, and end up getting ganked by the monster on the other side.
As for your points one and two...
1) The healer of Ilsare doesn't have Raise Dead or Ressurection. At least, that's how it's RPed. The real reason is that it's an AI. It won't res you on its own; it has to have a DM Possessing it. You have to work around the mechanical issues, here.
2) Yes, the town guard would really allow an orc to get into the town. First off, he's bloody useless and overpaid. Secondly, there are enough orcs on the side of the former Dragoncalled that it tends to raise fewer eyebrows to let an evil orc in, and kill him once he does something bad, rather than slaughtering every orc one sees.
As for the gold, och. That's nothing. You can get that much easily in the Crypts in about ten or twenty minutes, regardless of class or level (though class and level do affect how long it takes).
