UPDATE:
I went to a couple stores and got some quotes, this stuff seems to be about $270/square. Probably going with Certainteed, Double 7" straight edge perfection shingle. Sterling gray matches the SITB color nicely.
They have vinyl door and window casing that is 2.5" and accepts the siding FTW.
-10 square of siding
-25 lengths of 3/4" j-channel.
-.5" R3.3 4X8 insulation (Tuff-R-F1s, 30 sheets).
-Mitered outside corners (looks like shingles on the corners, this added about $300)
-4" starter strip
-1.75" roofing nails galvanized 50 lbs.
$4,228
A lot better than the $7,800 quote I got to have it done and that was without mitered corners, he was going to add $900 for that, lulz.