I like a mix of needing cosmetic updates and basically turnkey.

Basically I am trying to understand what is the risk behind so many "No Section 8/DSS" postings for rental properties. 

Worst case scenario the previous owner used to own both properties before the one further back was seized, so I'm pretty confident under existing precedent that the courts would grant me easement under unity of title and necessity.  

Basically the plumbing and heating need to be fixed for sure.

But all the times I went to court and saw other landlords get their evictions denied, the two biggest reasons were 1) not delivering proper notice and 2) accepting partial rent. 

Every jurisdiction while following perhaps the same basic laws works a little differently. 

This basically made a lot of SFR or duplexes being used as short term rentals limit their income potential and made the income on par with what you could get with long term tenants. 

In the most basic terms, the pros have experience renting out properties and vetting tenants, handling repairs etc. and take all of that off your plate, with the con being that this costs money thus lowering your return. 

My mentor gave me a list of about 70 target houses in the area, which I have since door knocked and dropped off fliers.I figure the process of finding a ripe deal has a basic system.

Then he started refusing my rent until I agreed to pay what I had just proven was paid and the court told ruled for me because you can't refuse and return rent, the turn around and sue for non-payment (duh!).