You should be able to take a ladder and wipe away a little snow to get an idea of the shingles such as layers or age.

There were no other deals brought, other than mine.The other meet up i went to was $10 and also was a "bring your deals" and mine was the only deal. then a lady spoke about shingles for an hour.

Yep when you hit the brokers side and hang your own shingle you will look at it from a different perspective.

He also said the roof was leaking because one shingle needed to be replaced, but that did not explain why every room and bathrooms in the upstairs had water marks running down the walls.

These wood shake roofs are now unlawful in the Peoples Republic of Kalifornia to install, BUT, will a lender lend on a home with an existing wood shake roof that is in servicable condition in a lower risk area, to wit...

So others seem to have assumed asphalt shingles.

At first it was hard to see them because they are mostly black and our shingles are black, but as I looked closer I saw hundreds of the things, mostly on one half of one side of our roof. 

. ;) she had also had the shingle roof replaced, new siding and new replacement windows done before she got sick.   

Are all three pulling their own permits, doing complete year off and new, and quoting the same quality of shingle, same amount of felt/Underlayment, etc?

It's 3 tab shingles not architectural.