Yes, a lot depends on point of view; as Gareth says, Arnold is a good example. Afterwards he lived in New Brunswick, among Loyalists who moved north. Of course, they were all renegades to the people south of the border. His plan was not so much betrayed but stopped by dissention among those who were to surrender in the deal. Benjamin Franklin spent time in Montreal trying to get the sympathy of the inhabitants- even set up a press there, but unfortunately the Colonial troops in the region, without real leadership, were a bunch of drunkards and looters, so he left empty-handed. Otherwise, the area of the initial United States might have been larger.
I agree with Art Thieme up to a point. The songs reflect the passions and the humor of whoever wrote them, and those whom were like-minded, but may not have reflected any concensus. They may be documents but they must be interpreted within the context of history. Unfortunately, much of our primary school history teaching reflects the current bias of the teacher and the views of the people in the area where the school is located. More considered viewpoints are obtained only at the university level or in individual study.
Songs do reflect areas, but only to a certain extent. The area of old songs was, as you say, in the southern mountains, but also in the piedmont and coastal areas, where people settled early and stayed.
The cowboys of legend worked from Mexico to the Dakotas and Montana, moving Mexican and Texas cattle to the railheads and to the Indian agency camps (the real area of the buffalo hunters on the old Sioux, Cheyenne and Arapaho lands mentioned in the "Buffalo Skinners"). Bias and ignorance causes us to overlook the area and songs of the vaqueros in our southwest as well as the early cowboys in Louisiana (Acadian, largely). Mexican beef was regularly supplied to the drives.
The earlier lumbering songs would be from the area running NE-SW paralleling the east coast from eastern Canada to Alabama and Mississippi, west to the Ohio River and south to the pines in the sandy soils of east Texas. Nowadays we think only of cutting in the coniferous areas in the northern tier of states and the surviving west coast forests. "The Pinery Boy" is more a song of the raft, barge and boat people of the river and lake systems who moved cut timber among other materials. Our oldest known lumbering songs come largely from New England. The northeastern area, including Ontario and Quebec, remained harvestable for white pine and other timber until about 1900.