How much room does your packable rain jacket take up, and what shape does it pack down to? That might be a limiting factor on what bags would work well for your load.
The Pilot might work for you (depending on how the rain jacket packs down) but it doesn't compress very flat. You might want to take a look at @bouncing's post Could you fit a Pilot inside an Aeronaut 45? for some discussion of that idea. Your Tortuga Setout may have a different pocket arrangement that makes it easier to put a fully-packed Pilot in the backpack than it would be to put it in an Aeronaut; I'm not familiar with the Setout.
How do you feel about using a Daylight Backpack and adding a Cache or another laptop sleeve to provide padding? I think the DLBP (Daylight Backpack, not to be confused with the DLBC or Daylight Briefcase) probably wouldn't give you the Dora the Explorer look you want to avoid.

The Luminary 15 isn't as packable as the DLBP. I'm still thinking about whether I think it would hold your items easily; its shape might mean it doesn't work as well for the purpose as a DLBP or a Pilot, or it might mean it would work better. Let us know about that rain jacket!
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