There are some deferred maintenance items like a leaking HVAC against the back wall, some shingles in need of replacing, and a dent in one of the walls.

The building inspector did mention the property was well maintained and he had mentioned that some shingles are missing, he was not able to guess the roof life so he just referenced the disclosure and put the same age. 

So my tenant calls and tells me, that she thinks the tree in the neighbors yard is damaging my roof because she saw some shingles on the ground in the backyard.Needless to say, I go over there to check and from the ground I can see the tree branches are actually touching my roof.

Well I do some research and speak to his inspectors and it seems this lawyer jerk was up on my roof poking the new shingles with a sharp implement and it caused damage to the shingles. 

What we didn't know is that the existing roofing material was an abestos based clay type shingle (sellers didn't either). 

A few broken shingles here and there, curled up shingles, damaged skylight frame window.2) Mold noted on the basement walls. 

New siding melted in summer heat - instead repainted old shingles on front of house.

.#3 Contact Local Contractors for PricingCall local Subcontractors and get budget pricing for common repairs on your typical rehab project.For example, call a roofer and ask what their average cost per Square of Architectural Asphalt Shingle Roofing would be on a 1,500 sf house, with a 6/12 pitch.Note: Some contractors will be reluctant to share pricing without seeing the property, but tell them you are just looking for a rough budget number you can use on future projects.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

I won't go into the the story because it's long, but basically there's not a claim to be made due to a warranty issue with the shingles and the manufacturer refuses to pay the claim.

It appears the shingles are drooping notably at the ends of the runs in certain areas, possibly hiding at least one layer of old shingles.Your interior pics do not show any concerning areas of leakage or mold.