If that is a shake roof, replacing it will also need all new sheeting underneath the new composite shingles, since there was none with the old shake roofs. 

It has the original Cedar Shake shingles with architectural shingles over top.

I got there and noticed the leak, looked around the outside for a missing shingle or anything obvious.

It's essentially barn board that is gapped a few inches and over this typically cedar shingles were installed. 

I was able to find a great contractor with a 30 year transferable warranty (we didn't use regular shingles) for 22k and he got it done by the end of December last year.

I don't think it is a materials breakdown like nails, shingles, felt, etc.I think the biggest question you have is if the price is fair...maybe.The cedar wood you talk about is cedar shake shingles?

There a quite a few post-war (1946 - 1955) houses around here with 9/12 or 12/12 pitched roofs which are still sporting the original steel.You can paint them, but unless you expend the effort to prep the metal, the paint may not stay all that long.If the roof is near the end of life, consider replacing it with a new steel or aluminium roof .. they will last 2-3 times longer than asphalt shingles.

Got 2 reply from roofers, they found significant hail & wind damage to the roof which contains x2 layers of shingles and can not be repaired.

It's on a cinder block foundation and has a shingle roof in good condition that an assessor said looks to be about 4 years old.

Shingles and gutters.