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. 

I started doing some home flipping from 2001 - 2009, then got into buy and hold.I am at a cross roads, so I recently sold some properties, in an effort to have a portfolio of quality over quantity.Not exactly sure what my next move will be, the big challenge for me has been learning about tenant issues, and dealing with some unexpected repairs, both my wife and I took a course and are IPOANS CAM Certified (Certified Property managers).We only manage our own properties, plus have a couple of hired property managers to help with some out of town units, however, I have been studying tenancy rules, laws, and have become addicted to answering property management questions.What attracted me to join this site, is all the different types of real estate investment people are involved in.I look forward to participating in the forum.Michael P Currie