RyeThomas

I own a small roofing and siding company. I had the same delima and went with Certainteed shingles, and James Hardi fiber cement siding. Now being a contractor I got everything at cost so my architectural shingles are their top of the line and a little pricey for your average homeowner. But Certainteed has a shingle called the Landmark, by far my best selling shingle. Very cost effective, it is an architectural 30 year shingle. They also make the Landmark TL which is alot more money but again it is a good value.
If you use a good paper and Ice and water shield as per code you will be fine, and have no ice damming. I used a Titanium paper, a PIA to install but it works very well. I also used Ice and water shield around the entire perimiter, the ridge, and of corse the eaves as per local requirements.
As far as siding Hardi makes a board and batten but it is not cheap. But fiber cement siding is very strong, and resists the Hail storms we get here in Northern Virginia. Any questions feel free to PM me.
And as far as metal the price was high, install as my roof is pretty cut up was gonna be tough and with all the ridge I have it just didnt pan out.