Yes, an asphalt shingle roof will eventually wear out, but expensive roof repairs generally stem from not replacing the occasional shingle blow-off or failing to put $5 of roof sealant at flashing areas.

But again, this is all being recorded at city center surrounded by 10x population, asphalt, cars and ac units that didn’t exist 80 years ago.

We currently see ourselves holding it for 20+ years, but life tends to throw curveballs so we may go with the cheaper asphalt option. 

So all but that one window is installed.The main roof, which is asphalt shingles, got installed.

Be prepared to pound the pavement.

.#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.

A roofer might be able to tell you that they can install asphalt shingles for $150 a square as a ballpark figure.

I'm continuing to hit the metaphoric pavement so to speak - reaching out to more folks until someone at least will process an application - but it seems official policy is to not process mortgages for investment properties.

@Brandon Capelle Where Exactly is your property line, in relation to the edge of pavement.

I will circle the building looking for parking, general condition, cracks in pavement and building, look at the cars, any abandoned vehicles, size of dumpster, garbage around the container etc.