Very nice house Nick. I don't know anything about roofs, but sure know a few friends/old neighbors that had gotten a bad deal by their roofing contractors. I dread the day when its our turn.
As mentioned, I have the advantage of my wife dialed into the local contractors.
My experience is to search out someone who is local and has some history. If they don't do well locally they will not last. The guttering company my wife works for is a cash or check business and requires a surcharge for a CC payment. The heavily advertised gutters/gutter guard and roofing companies will also offer financing which is their draw for many that require that service. If you are ready to pay cash or write out a check the local, small business is the way to go for price and quality.
I based my contract on personal recommendation and not on price as there are many who are not licensed and just pick up workers at the local day-job location. There are many who will undercut price but I feel the quality of the work will suffer.
My reason for this topic was to inform others who have had architectural roofs installed a decade or more ago that there were lots of them installed incorrectly according to my contractor. It appears to be so as I saw my neighbor have to replace part of theirs on the backside of the house because of a leak.