Here's how you play him now (if you don't want to auto-fail his mission). Go to Innsmouth asap. Use the location encounter that lets you search for research materials. Get one or both of them. You can now either seal an OW with that as your "fifth clue" (it won't cause you to fail your mission) although it's a bit risky because if you get a clue that tips you over four, you'll fail his mission. (Of course, it's easier if you just get an elder sign at the beginning, but, heh, that requires a bit of luck). ::Shrug:: anyways, if you deliberately close a first gate with him without sealing it and then have him seal a second gate (with a research materials or two— if you're feeling especially cautious). He should be able to get a permanent retainer by turn eight if you do this. It's not that bad a tradeoff.

Ok, here's what I think of Darell's story..

...... Darell doesn't want to be in gates anyway. He never did. If Darell is in a gate, its just wasting his awesome Town encounter ability. I would just ignore Darell's story completely and do my best not to either pass or fail it. Darell can contribute to the game in a lot of other ways, getting other characters money, items, doing Missions/Tasks or having encounters at the Cuiositte Shop to pick out a favorite Unique Item. I wouldn't send Darell into an OW unless things were looking really bleak. His personal story doesn't encourage me enough to do this.

Making Darrell jump through hoops for his retainer is a definite hurt. If you're interested in passing his story, it can be done without putting your game in too much danger, but it's a lot of trouble. It's a story that's really easy to fail, though, and a shame if it does. It's easier to send him around Arkham (incorporated) to do his thing. Tasks, missions, Kingsport, calling the feds into Innsmouth, things like that.