It's been there for 80 years and the roof line is straight?

Just for potential notes: going by the numbers, the 4plex doesn't seem to have separate electric meters, both the fourplex and duplex looks like a roof replacement is due, some windows are boarded up (100% occupied)driveways would need to be added (currently a dirt lot)There is definitely room on the property to add another 4plex if zoning allowed (there is an apartment complex right next door so I don't see why not)even the third property has a good chunk of land behind it considering what the norm is here.There is a nice elementary school that is just being completed on the same street less than a few houses away.

Another aspect you have to really consider with websites is the conversion rate.  

Too busy to keep the roof over their head?

A good flipper employs these aspects even if they don't really understand what they are doing, a bit of luck and common sense sometimes prevails. 

Welcome,I've been involved in the construction/trade aspects of RE for the past decade.Let me know if you experience issues getting the right guy for the job and I'll see what I can do.My RE experience and knowledge are limited, but my optimism isn't.Best of luck!

people living under the same single fam roof/dwelling don't routinely collect RENT from the rest of their family as  LANDLORD-TENANT relationship(s), even if it is their MOTHER IN LAW =Dthus, while the house may have a grandfathered (or grandparented to be more PC?)

Im trying to learn as much about all the various aspects of investment, as we live in a one size does not fit all world now, adaptability and creativity are key to me, in understanding what are the best ways to handle a real estate investment opportunity.Im here to learn and network with other investors so I can take advantage of the wealth of knowledge and turn it into a sustainable business. 

If you have 2 identical homes, one renting for $500 and the other $1000, replacing the roof is going to cost the same it won't be cheaper for the lower rent home.If the buy, live in, fix-up, then rent out works for you and you are comfortable with that strategy why not stick with it. 

You'll find plenty of homes with little to no roof left.