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I thought that business with "the appropriate henchman" made sense too, since each hench so pointedly tells you about a certain area. But the fact that they know about an area is not what makes them appropriate for that area; it's their skills. Always. I mean, who cares what charm and connections Sharwyn may have in the Blacklake-- she's not going to talk to anyone and introduce you, or make any inroads on your behalf.
If there are traps in an area, you need Tomi. Period. Doesn't matter if you're in the Tanglebrook Estate in the Peninsula, or Meldanen's Estate in the Blacklake; Traps=Tomi. In the Neverwinter Zoo, on the other hand, you might want to have Daelan around, as the guards tend to swarm you. So talk to Tomi, and tell him to part ways so he stands right outside the Zoo. Then use your Stone of Recall to go back to the HoJ and pick up Daelan (oh, yeah, first thing you should do is hire all the henchmen-- one at a time, of course-- and lead them to the HoJ right near the recall portal and then part with them so they're all right there already. Saves trekking back and forth to the Trade of Blades), and portal with Daelan back to the Zoo. Do the Zoo with him, go outside to where Tomi is standing and then Recall Stone back to the HoJ, drop Daelan, portal back and rehire Tomi.
Done. Get used to switching henchmen a lot, if you're going to use them, and get used to re-doing areas, as you kinda have to go through the place once to get the lay of it and see which hench you actually need to get through it.
Hope this helps.
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