(Roof, new sewer line, new appliances, etc)

They may have had a negative experience or feel that way because of something, but everyone is different and the more money you can bring in under one roof the better hence why I believe that MFR especially the smaller units are your best bet.

I believe in larger cities, where you find most 20plus units the city makes you have an onsite maintance person or PM, check with local laws on that tho.To me 20units under one or two roofs is completely different than single homes.

We are looking for a good General Contractor to help us along, as well as a good roofing company, and possibly sub contractors in flooring and bathroom/kitchen remodel.  

I bought the house for 53k but then I had to pay for roof replacement (4.6k) and some repairs (6k - paint, cleaning, new appliances, insurance first two months payment and more).

Roof, Electrical, Plumbing & HVAC.    

A huge hole in the roof for years is just a giant unknown.What can make a property a lost cause.  

This usually makes a significant difference, because the tenants forget to turn them on, and now it will automatically come on.You should also check the vent outlet on the side of the building or roof and make sure there is actually air flowing out.  

This ALONE is about 50KYou have not even touched electrical, plumbing, painting, roof, hardware, furnace, water heater, landscaping, I seriously doubt the repairs will be 75K

Nothing good was coming up locally so my wife stepped up and it is working out great, all under one roof, good class of tenants and well maintained=not too much work.