Information on all skills is so far, sparse. We know that survivability and abundance of resources will be determining factors of the 'where' settlements are placed during D&SS,and therefore will play a role in where future settlements are built.
I expect being a full-time explorer will provide you with little and less than the comfort of a town does. You'll probably have to pack trail rations or scour the wilds for food and water, shelter will become necessary during certain seasons in certain biomes, and there is a limited carry capacity. Given that we know you won't be able to fully "master" some skills you haven't practiced in on past PCs, an exploring team will probably cover more land, and provide a more quality map or more scavenged resources. There is strength in numbers after all!