IF you could inbox me your credit score and credit issues it would be helpful.

My default position has always been, "No one will take better care of your property than you".However, here's a list of issues that can force you into using a PM:Out of State - non local propertiesRE inventory that requires too much of your personal timeSpecific properties with a unit count that then require onsite managerIn Calif, (3) the count is 16 or more units, and if you hire a manager, then you have to follow all the employer regulations, which easily adds 35% above the salary. 

Sorry to hear you're running into issues like this.  

There's some issues buying there for buy/hold and getting cash flow with rent control.  

Schooling in my town is amazing, so there is no issue with that.Transportation to NYC is literally 2 minutes on every corner to the bus, so that isn't an issue.Additionally, I was told that I should stay away from homes with oil tanks for heating because if the oil tank was to leak, the soil would be contaminated and it would cause a big headache and a big whole in my wallet.

You would probably need to issue a W-2 for your wife.On $100K, it likely will not provide a huge benefit to add your wife, as you would likely not max out contributions in your own name, but having her as a documented employee of the company would allow her to rollover existing savings from another retirement plan into the account.

Unless the house has serious issues. 

Period, So, they weren't making a judgment about the viability of my particular deal.As to the "break-even/lose" issue - well, I've learned so much while working on this house.

Biggest issue is that 2 of the buildings have history of flooding.

Most of those issues can be learned from and addressed in the future.