Whether they have civilian gear or military is irrelevant - there will certainly be surplus military gear around, so a given traveler could easily have either. If it exists as an item of non-Morrow equipment, there is a plausible reason why a given traveler could have it or not have it.
The biggest problem for the contact person is not their gear, it is (at least the first time around) coming up with a reason why they are travelling in the first place, and explaining their inexplicable lack of knowledge about certain subjects. Remember, the contact person is not an emissary to some newly discovered aboriginal tribe, they are a distant cousin of that very same tribe, expected to share a certain degree of communal knowledge and experience.
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