Talk to Todd *while sitting down on a barstool* each night he is at the bar until the action icon is grayed out, and each night he is in the nightmare. He's the guy with the leather jacket and pompadour at the bar, and is always with Archie. He will be there on:
Day 2 from right when you start until 21:45, about 2/3 of the way through the night. Answer: "Maybe..."
Day 3 from 21:35 to 22:15. It's later in the night (over halfway), and they aren't there for long, so make sure you talk to them when they are! A: "Lots of money."
Day 8 from 21:50 'til closing time. You can't miss this one, as you are allowed to linger as long as you desire.
You also need to talk to him each time you see him on the landing during the nightmares. He is the "Sheep with Regent Hair". Just be encouraging here; the answers should be obvious. But let me know if there's one you aren't sure about.
NOTE: I am 99% certain I gave a "wrong" answer or two at the Stray Sheep, according to the wiki, and still popped all the helper achievements. I include the answers so that you can be on the safe side, but you may very well be able to answer however you like. If you have confirmation of this, please comment. If you want to be safe, answer as posted above.