Short answer is no, your not going to get a line items detailed break out on a quote/Estimate. You may only see that if your dealing with an insurance claim, and then the totals will be high, which is probably what pricing the 2 companies you mentioned are using! (ins #'s to get their final price) The Est's you shared, ARE High!!! And surprising you are correct on your own assumptions... $20 on the high end. :) That is, if it is truly 1sty, Non-Steep, 25sq, Total ReDeck.
Dan had a good suggestion (but reading his comments, I see why he doesn't do roofing anymore (lol)), to ask a local Supplier for a reference. But, if you want to cya (cover your a*s), and require them to have insurance, long warranty (5yrs), etc... you won't get a "crew" but perhaps a good owner/operator. "Crews" don't have their own insurance, generally. And again, no line items so they won't be quoting you price per/sheet of plywood or osb, because it is ALL being installed! (cedar shake shingles being removed, solid decking being installed) = a ReDeck job. IF it already had decking, then you'd see a breakout of: $xxx per/sheet of decking replaced.
@JD Martin : Kind of curious, WHY would you use 4 different contractors for roofs? Did each one close shop, or you were looking for the cheapest person each time? ... If your an Investor, your the type that "we" usually try to avoid for sure! lol Nothing personal, but the Investors that we work with, know that WE are trustworthy, do a GREAT job, and we are very fair on pricing. So why wouldn't they use us on other jobs!? :D
Suggestion: On a total ReDeck, spend the little extra and get the OSB boards with the Radiant Barrier on the back of them! (like aluminum foil) When newly built or situations like this, is the only time you get to do this! And here in the South, we build or always think about ways to reduce or alleviate the Heat! Maybe you don't have to worry about that so much up north.
AND, when they strip off the cedar, you'll have the lathe boards up there (1x3's or 1x4 boards), most time the crews want to just move the few in place to catch the edge of the new decking, BUT go ahead and tell them remove all the extra ones! So you'll leave the ones up there that need to be on the edges of the decking, about every 4ft, coming down the roof. Do this Especially if your going to use the Radiant Barrier decking, as any surface of that stuff that is pressed up against something, I.e. the support lathe boards, is negated! (if pressed up against something, the R.Barrier doesn't hardly work)
Sorry I/we aren't closer to help. For sure, don't call anyone that you might hear on the Radio, see on TV, etc... There's a reason they have the money to spend on those expensive ad slots! :P Message me directly if you have specific questions or that.
Jerry w/J's Roofing Richardson, TX