About the only thing decent on this house is the roof, decking and shingles replaced in 2009, still dating the shingles pretty old.

On pitch roofs, how old are the shingles?

The buyers were afraid of asbestos shingles ( Ni big deal) .

You don’t want 100 year old homes, you want 20 year old homes, or newer.You don’t want property taxes approaching $4,000/yr for a $400k house, you want $2,000/yrYou don’t want a home that is subject to hurricanes, flooding, tornadoes, earthquakes or snow stormsYou don’t want states/areas where insurance is routinely over $2,000/yr when it can be found in other states for $600You don’t want to be in a state that takes 8% of your income in state tax when other states take 0%You don’t want houses with siding or roofs with shingles or yards that need maintenance when stucco/tile/rocks exist You don’t want states that make you pay to remove a tenant, or deny you the right, when other states make it “easy”You don’t want a city/state that tells you how much rent you can charge or how much you can raise it while not limiting expenses.Those are the givens… personally I add you don’t want your tenants sharing a wall where you have tenant on tenant complaints.

As long as your support system is sufficient all you're doing is creating a floor inside the "attic" that's covered in roofing shingles instead of plywood.

Most audits are just computerized inquiries and rarely get to the level of an IRS agent coming in person.

I just hooked up with a company called Shingle Tech. 

.#3 Contact Local Contractors for Labor Pricing / Hire a GC to ConsultCall 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.You can also pay a General Contractor a consulting fee of a couple of hundred dollars (per house) to walkthrough a few properties with you and provide a detailed estimate of prices that you can use as your 'menu for 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.

Have the roofer look at the area where you noticed the leak and have them pull up the shingle to see if a nail is causing the leak.

The roof is asphalt composite shingles.