Well I did some homework and found http://www.cleanenergyworksoregon.org/ which is a non-profit that will do an energy assessment and make recommendations for my attic/insulation issues. Thanks for the suggestion, Handymac. The program is reputable, and associated with EnergyTrust of Oregon, who do most of the Tax incentive work around replacing older appliances and adding insulation, etc in Oregon. They will then refer me to a couple of contractors that are OK'd to do the work by their program, and qualify me for any tax incentives, etc. That way I have a better idea of what is needed/ideal and can get bids to compare apples to apples, so to speak. Mainegrower, you've given me pause to think about the chimney. I'm not convinced that I should NOT remove it yet, but giving it some further thought. The chimney runs through the laundry/bath/pantry area the back of my house, so I'm not sure how useful it would ever be as a heating chimney, but I'm doing some additional looking into it.

So, I have an update. We had a new contractor come by and he said that my pitch is too low for metal and he would suggest EPDM rubber roof. He said it would have 1 seam. He also said it's commercial grade, they put it on restaurants and stores all over town and it will last longer than the Certainteed Flintlastic that was originally proposed - price is $2800. I should also mention that these folks do a LOT of work in our area and they have great reviews on Angie's list. Here's the contract wording: Proposal for high density board and EPDM rubber membrane. New 1" ISO insulation board to be put down over entire roof with 4" screws and plates 12 to a sheet. 0.60 EPDM rubber membranes to be installed with a rubber to substrate adhesive. All rubber to rubber seams to be installed with a 6" seam tape then caulked with a rubber lap caulk. Projections through the roof to be flashed with a 6" uncured flashing roll with a termination bar anchor strip then caulked as per rubber spec sheets. New painted gravel stop metal to be applied to all roof edges. Gravel stop to be counter flashed with a peel and stick self adhesive 6" cover strip. Does this seem OK? They offer a 10 year warranty on their workmanship and I think there is a warranty on the material too, maybe 20 years?

I'm in the northeast with a house that has the same combination of cathedral ceiling and attic spaces. Our problems are probably yours times 100. I agonized for a year over how to re-roof and insulate, and ended up going with the smartest roofer I interviewed who said, basically, you are far better off spending money on circulating air with fans than in trying to improve the insulation in the roof. I don't know if this is at all relevant to your situation, but at least it should make you feel better. I mean, how bad can your temperature shifts be in Hawaii??

Dear Groveraxle, Thank you for this article and your comment. I was thinking the same thing. That said, our neighbors who have truly flat roofs always seem to be fussing with some of the alternative roof types described, whereas we've barely had an issue with our old shingle roof (until a tree branch shot through it). I think the metal would be nice, but with the trees dropping branches, I think the metal might fare worse than shingle. I've debated going with the very flat and cheapest three tab type of shingle, since essentially it's the plainest, but I'm told the "landmark" is a better product...