The new roof is on! It isn't quite as dark as I would like, but Jeff made the insightful remark while we were considering shingle colors that a midtone would hide the plenitude of pine needles that reside on our roof for most of the year. Color is a secondary concern, anyhow; the best part is that it's new and clean and practically free!
We debated whether to upgrade to an architectural shingle (which adds such a great texture and dimension to an otherwise blank, nondescript plane), but we decided it wasn't worth it in an older neighborhood like ours given the relatively short time we will probably dwell here. We will see about painting the trim at a later date; again, something that probably isn't going to happen unless we're here longer than we think.