@Matt Hummer,The distinction I'd recommend making is between what you are allowed to do legally and what you should be doing based on your skills and knowledge.If you are as competent as the professionals you would otherwise hire, then weigh it against the value of your time versus the cost to hire it out.

York is the 11% least safe city in the country and has been in the top 20 most dangerous cities list for as long as I can remember.For comparison, York had 75 shooting deaths in 2016 for a city of ~43,000 people.

I work with homeowners who are a little behind on their mortgage payments and in danger of losing their homes.

Drug dealers and dangerous criminals roam the streets.

I know this woman is in a rough spot (from your description), but do not make a renting decision from your emotions... it will come back to bite you in one way or the other.You should have your own 'qualifying criteria' and one of those should be that the renter grosses 3x the amount of rent every month.And I am unclear if that is a rental judgment that has been paid or if she was evicted... it is possible but would be really rare for their to be a 'rental judgment' on her credit report without it having gone to court.AND if she still has medical bills to pay, it seems like you are putting yourself in a dangerous place.AND, yes, you would have to go through the normal eviction route costing you more money, time and hassle...

That is most dangerous city I've ever lived in.Outside of that, however, I don't agree with using property management unless you are at such a level where the hefty cost is justified.

These are important distinctions and you really have to continue to study on sites this this as well as talk to other experienced investors who have purchased turnkey properties before to know exactly what to look for in a quality company.  

Current Situation:As of today we have executed three separate deeds and have separated the parcel into three distinct lots.

You're in big trouble.I can see the dangers of leverage when there's no money down.

New Haven has very distinct neighborhoods.