Make sure the contractor puts on 0.048" thickness vinyl siding and not the typical Menards thin stuff to replace it, because that's what your insurer should be paying for at minimum to replace instead of the aluminum.The roof is iffy - it depends on your shingle type and carrier.

Well, if this is the conclusion you reach, then the move to automated and computerized and remote and desktop, etc, might make sense.

At the same time I've had 3 roofing companies come out and see if they can repair it but due to it being an older home and double layered shingles they all said they'd have to replace the whole roof.

I am not sure where you are in the country, but you could likely take the necessary test prep, take your exam and hang your shingle with a broker in a month to 45 days.    

Both buildings are very well-maintained with unique all metal roof & shingled siding as well, so offers low exterior maintenance.

There’s no mention of the roof age, so I’m assuming it’ll need replacing soon, especially since the edges of the shingle are curling.

I painted the Exterior of my house and put shingles on a shed out back new sink and other cosmetic stuff.

Flat roof or shingles, the sooner the better... winter is a coming!

The owner must grant such access to computerized orother electronic records & to any computers, facilities & mustprovide any information or assistance needed to access the records.5.

Anyway, the stack coming out of the roof if a big metal rusty mess that has been staining the shingles over the years.