As long as the property is performing, the vast majority of the time, you are better off doing regular maintenance vs. waiting for something to break / fail be a problem that could escalate to a crisis (nothing like a sewer line back up!).

I am a three your major in self directed studying of Real Estate investing.

My mindset is that it is low risk when the majority thinks otherwise but I have many years of experience in Detroit.

Simple, the majority of renters (48%)  reside in the city and the vase majority of people in the suburbs own their homes. 

You are all right in the sense that if it's a major job what was once a promising little cashflowing property can soon become a money trap or worse, a black hole for my money.Cheers!

Are you finding good velocity of deals at the higher cap rates, or are the majority you see at the lower?

Subject property is a 14 unit complex,  built in 1980s,  decent condition with no major repair anticipated.  

However, I also see plenty of threads where people (including myself) who have actually tried to follow that advice, have run into major roadblocks with financing, taxes, and even insurance.

Long term... its a little scary knowing that these buildings are so old and may need major replacements roof/siding/heating or air.

Roofs maintain the integrity of the rest of the house and should be maintained as such.The price in which you purchase the property should factor in the age of the major mechanics along with windows, roofs, and siding considering where they recommend in their life cycle.