It seems like ½ the houses in this town are missing shingles and some of them are missing A LOT of shingles.

If/when I re-roof, would it be better to remove the metal and put composition shingles?

I've done both a rebuild and just re-shingling on historic buildings - the rebuild ran me about 20K, which included the new shingles and gutters.

The house has a 15 year roof (the "flat" looking shingle tabs) and the roof is now 19 years old, so over its life expectancy.

I havent seen it yet though, had a house with painted wood shake shingles that they made us touchup 3 times because the paint wouldnt stay stuck to the damp shingles in November.....I told my partner once I was going to put a hole in the wall directly across from the entrance so these inspectors could feel validated with their job.

One side snaps to the gutter and the other side gets shoved up under the shingles.

Extent of rehab would be interior demo, new interior finishes, asphalt shingle roofing, vinyl siding and landscaping improvements.

Surprise under 2 layers of shingles had to re-sheet roof Winter weather and contractor delays Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

It's a gable roof with regular asphalt shingles.

Ever since then, we've been contacted by multiple roofers who work the insurance angle (we can get you a deluxe roof for your deductible, etc.).Here's the thing: the roof is original from 1978 and was trashed long ago - shingles were already peeling, vines had wrecked havoc, gutters are falling off... this thing needs the works.