As a general rule, how far would you say OUTSIDE of a fortified settlement (say a small walled city) would be safe?
It depends, but for a typical "points of light" setting, I would argue that a good rule of thumb is this:
1) Within the named settlement that makes up the point of light, is considered 'safe'.
2) Farms/hamlets and other small settlements within 1 day's travel from the PoL is also considered 'safe'. In order to keep its citizens fed, the PoL has to patrol these areas reasonably well. So, if you need help you
don't have to travel to the PoL and back - there's probably a patrol or small garrison within an hour or two of travel.
3) Farms/hamlets and other small settlements within 2 days' travel from the PoL are a 'grey zone'. They're markedly less 'safe' than those within the 1-day boundary, but they're also markedly more 'safe' than those without. There will be far fewer patrols in this area, but the people themselves will likely be a hardier bunch, and more apt to travel to the assistance of their neighbours. This is very distinctly a frontier area.
4) Anything more than 2 days of travel from the PoL is considered the wilds.
Large cities will necessarily expand the radius of the various rings - say 1 day/2 days for a "Keep on the Borderlands", 2 days/4 days for a medium town, 4 days/8 days for a city?