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. 

I strongly recommend you take your time to learn and to find what interests you before making any major decisions.  

But this area lacks a major grocery store, movie theater, chain restaurant, etc.  

I did use a contractor to help out with some of the major repairs (42 windows, brand new plumbing, new hardwood floors, and converting from radiators to central air) the rest I did myself so I got exposure to working with contractors and truly understanding what kind of work is involved and what some of the costs in a rehab might be and how to survey a property for needed repairs.

There's a major rezoning coming here, most likely beginning in 2015, that's going to be boosting development density to 260% of the current base permitting, going from 22 dwelling units per acre to 58 and raising height limits from 45' to 75'.