I would ask the owner for the age of the roof, age of utilities (water heater, boiler/oil tank), and ask if/when the most recent upgrades were made to the property.Of course, take the responses with a grain of salt.

I would check roof and structural damage as tornado 2-3 years ago tore up this area pretty bad. 

The seller was moving to NY and wanted an as-is sale right away, but wanted to have the ability for his family to stay in the house for 2 months until school was finished.The house was pretty nice, just needed a cosmetic update inside, and the roof was shot.

Cash flow is definitely important (and I don’t know your finances) if you need to replace something major like a roof and you’re never making that money back.

I just keep plenty of cash in the bank and I don't worry about it.Have enough for a complete HVAC or roof and you should be fine.

All but 2 of the properties need cosmetic work only (I am a General Contractor so can do most of the work myself). 2 properties need new roofs and I have a few roofers to do the work.

BP has lots of good books on many aspects of real estate. 

Our ideal property is single family home, ideally less than 20 years old (willing to budge if major upgrades we're made w/in 5 years, such as HVAC, roof, etc) within a 30 minute commute from uptown Charlotte.

I replaced the entire exterior including roof, soffit, fascia, gutters and siding and some windows.

Renovations included complete exterior: roof, gutters, soffit, fascia and siding.