T2K method ... send a guy on a horse to the towns entry point, waving a white flag.
your questions a good one. how often do PCs come across a town and not know whether to bypass it or not? Most often my guys bypass towns. But as a Ref, often towns are neutral and have town based encounters setup, some of which might help PCs (resupply or story hooks).
In a T2K world, PCs dont always have the time or resources to take even a day working out of a town is friendly or not. If a town is "friendly" it might have defences setup but nothing obviously offensive, if women and children can be seen it normally means the town is not an all-male affair which is more likely to be dangerous to the PCs, and i think if you can see animals and vegetable patches then the town is more likely to be self sufficient and "friendly".
Whereas an all-male, offensively obvious (gun trucks!) town with no apparhent means of self sufficientcy (ie farming) is more likely in my view to be "danger" to our PCs. These are some of the "easy" and quick ways PCs might be able to determine if a town is worth visiting or giving a miss.
If you watch Walking Dead (I dont any more, crap) then the town of Woodbury would be interesting. Its defensive, cant see any obvious farming but i'm sure its there. Women and children present ... but might not be PC friendly. The best intel comes from inside the walls .... (snatch a town member and question them).
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