I believe the +2 applies to all settings, otherwise it would similarly have "in urban and underground settings" tacked onto the end of it, or at very least a second comma after "checks," or no commas at all.
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You will most likely not get direct interaction. They tend to avoid doing that on random posts, as it tends to create more problems than it solves.
For this post, you would indeed get the +2 universally. It makes sense, with those skill being honed while living in seedy locations growing up. Those skills would be useful surviving as a child and those skills learned would apply to all situations where being sneaky and snagging stuff applies.
I agree with Broadhand. If there were no comma, it would parse differently.
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By all means, post any questions you have here. There are a large number of seasoned Pathfinder GMs and players that are quite knowledgeable about the rules.
It is basically more community run process with explaining rules most of the time. If there is something ambiguous and unclear, then all folks with such concern will hit the FAQ button on the top right of a particular post. If enough people show concern, then their rules team puts it on their plate for looking closer in to. In general, if there are many folks giving consensus, then that can be used as a answered concern. The Paizo staff don't generally respond directly here. At time, you may get a writer chime in with their intent, but that is about it. The FAQ button is your comm link to the development team
