Assphalt shingling, brick foundation with vinyl siding. 

Find a reputable roofing company-look at online reviews and find one that has been in business for a while...ideally local company.Inspect the roof-are shingles curling? 

The particulars are:Total SF: 5160Roof: Shingles, replaced 2001Plumbing: Mix of PVC and Copper, updated in 2014-2023Heating/ cooling: forced air, 3 furnaces replaced in 2014-16, one AC replaced in 2014Electrical: has been updated periodically from 2014-2023.

For example a roof might have a 25 year shingle but with monitoring and minor repairs can easily last 30-35, maybe even 40 years!

He earned quick money as a wholesaler, and I have a house to keep)Rehab cost: $20k (vinyl floor, interior paint, new dual pane windows, new toilets and bathroom vanities, lights, new landscape, new AC condenser, all done by handyman, spent some extra money for minor plumbing and electric jobs, hydro jet sewer lines, clean up attic (had mice), added some insulationTime spent: 3 weeks (two handymen for the first two weeks, one for the last week)Value after repair: probably around $440kJobs still need to be done later: some dryrots, roof work (it's tile roof, roof doctor quoted me $9k, handyman said probably $5k, home inspector said $15k you can get a new shingle roof.

City had already approved a shear wall to ceiling but inspector dictated it go to shingles.  

Inspectors will check for leaks, sagging, or missing shingles, particularly in older homes.

Most homeowners think the wood is included with roof installs but more often than not, contractors just replace the shingles and maybe a sheet here and there so it looks like the wood was replaced.  

If only the outer roof covering (membrane, shingles, etc.) was replaced but none of the underlying roof system, it is not a restoration and you can expense these costs.  

Is the house a small two story with 800 sq ft of composite shingle roofing that needs to be replaced, or a large one story with tile roofing?.