A local roofer gets onto your roof before anybody talks about money. You describe what you are seeing, our roofer for this county reads it first-hand, and that same roofer prices it. The look costs nothing.
Two roof generations sit side by side here. The older core near the original grid has usually been worked on more than once, while the housing either side of a 1995 median is mostly still on its first roof. That is why two roofs a mile apart can need completely different conversations.
Inside the city limits a roof job is permitted by the City of Elkins, which runs its own permitting rather than deferring to Washington County. Arkansas has also required residential roofing contractors to hold a state registration since January 2022 for work above a modest threshold, and that registration carries a bond. Both facts are checkable, which is the point of mentioning them.
You get the materials named, the assembly spec'd to the maker's instructions, and the workmanship terms on paper before work starts.

