@Henley H.make sure you ask the New England guys as so much of our stuff is from the 1800's.  1900s is new :) This isn't really a fair analogy, but its friday...I might compare it to appliances....the new high end stuff works great, computerized, high performance etc. etc. but if the system is thrown out of whack its incredibly expensive to fix.

If there are cracked or missing shingles those need to be dealt with.

However, he installs new 30 year architectural shingles, Stainless appliances, hardwood and tile floors, newly painted interior and exteriors, and more.If you are going to own a property on a street of mostly rental homes, I'd suggest that you stand out from the crowd.

Removing asbestos/concrete siding/shingles falls into the easy and not expensive category and with a little preparation and 15-minutes of training, your average siding/roofing crew could strip and bag the side of a house.

At most, the judge may require the addition of wording to the effect, "Zestimate is a computerized guess - it is NOT an appraisal."

For a 1,000 sq ft roof that's $21,850....for the shingles.  

Usually you have to already be a realtor to hang the PM shingle.

I'd also be asking if the new roof is actually a "new roof" or did they just add a 3rd layer of asphalt shingles.  

Adding over a roof with a good dimensional shingle will not devalue the property one bit. it may reduce the life of it from 25 years to 20 but thats it. if its in really bad condition you may have to tear off the old roof but if its not it could save you about $1,000 in tear off costs.

Other houses in the same subdivision had no problems at all, but the houses built by that same contractor had foundation and roof (shingles) issues.