I think the pack should have well used equipment but have lots of options. It could have 300 items, but the specialist might only carry 20 of them if that is what the situation calls for.
I can see the specialist posing as
- A refugee
- A victim of local banditry
- A wandering tradesman
- A "bard"
- A messenger
- A beggar
- A person looking for lost loved ones
- A merchant (this makes more sense if the party has a horse)
Heck if they have good acting skills they might even portray a simpleton.
I always try to remember that the project expected contact to be five years after and had literally no idea what they would find, so I like flexibility.
Even though we had a 95% death rate there could still be a town with 10,000 people. That requires a different interaction plan than if you are dealing with the standard two street town as seen in so many westerns, where everyone knows everyone and a new face would draw much attention.