The cheapest ceiling fans I have found that are not garbage are the hunter brand sold at menards probably carried at other retailer also.  

Older properties carry a higher likelihood of systemic problems: lead paint, poly piping, aluminum wiring, asbestos, environmental issues, etc. 

Would the wrap around be: he still carries the mortgage of 44k, but we add to that (for example) a 60k mortgage that I'm going to pay?

I'd figure out what all the mortgage and expenses were on such a property, and assume a max vacancy rate I'd want to be able to survive, and back out the carrying costs in that worse case scenario.

A lot of the secondary market consists of people saying "I've got $50m and will purchase the next batch of Fannie Mae loans, paying 2% more than Fannie" -- so obviously that next batch goes into that MBS pool.That's what those people do now, but back then they decided it was more profitable to purchase crappy products than gold standard traditional Fannie. 

I have operated one of my 1-bedroom units in the city as an Airbnb for the past four years and it has literally been a gold mine.

I read on one of the forums here a few days back that a property owner requires that a renter carries renter insurance in their lease, but not require proof they actually purchased it.  

You want to carry EOA insurance.

You always  carry insurance on your properties.

To get to the point, I'd be doing scopes in Xact, which is the gold standard in insurance estimating.