Roofing in Cañon City
Cañon City is in Fremont County, not Pueblo County, and that changes who licenses and inspects the work on your roof.
Cañon City sits west of Pueblo up the Arkansas river, and two things make it a distinct market rather than an outlying part of the Pueblo one.
Different jurisdiction
It is in Fremont County, with its own building department and its own permitting and contractor requirements. A company perfectly properly licensed for work in Pueblo or Pueblo County is not automatically licensed here.
Since Colorado licenses roofers locally rather than at state level, this is the whole of the verification question. Ask which jurisdiction licenses the contractor, under what number, and confirm it with Fremont County rather than taking it on trust. It matters most with crews that arrive after a regional storm.
Older housing
There is considerably more genuinely old housing here than in the newer developments east of the river, and old houses hold surprises above the ceiling.
Plank decking. Boards laid with gaps rather than continuous sheeting. Sound construction, and modern shingles want continuous support, so a nail landing in a gap holds nothing. Where planks have cupped or split, overlaying with new sheeting before the roof goes on is often the right answer, and it is real money that belongs in the conversation before the roof is opened.
Multiple layers. Overlaying was standard practice for decades. Two or three stacked roofs is far more tear off and disposal than one, and a bid written assuming one layer will not survive finding three.
Get a per sheet decking price and a per layer tear off price in writing before anyone starts. On an older house here those two lines decide the final number.
A drier, sheltered pocket
Cañon City sits lower and more sheltered than the foothills south of Pueblo, and it is known locally for a milder winter than its elevation would suggest.
Practically that means less of the ice damming that dominates the conversation in Rye and Colorado City, and more of the ordinary plains combination: ultraviolet, thermal cycling and the occasional hail cell.
Choice
It is a big enough town to have its own roofing companies rather than depending entirely on Pueblo crews, which is worth knowing. Get at least one local bid alongside anything from down the valley.