For what I pay him, he will show me lots of houses, meet with contractors to get bids and even check on the progress of repairs in a pinch.

You will only attract the worst penny pinching buyers out there who will never respect you or your time.

If you get into a financial pinch, just refinance (no cash out), and you'll quickly be cashflow positive.

No sense in pinching pennies on something that will make your life much easier moving forward. 

If the apartment doesn't have one you really can't rent it legally and you will always be in the wrong if something goes wrong.If it wasn't for illegal in-laws a lot of people in the Boston area would be in even more of a pinch, but that still leaves you in a precarious position liability wise if there is a problem.

I do need to connect with more resources locally, that's a goal of mine. 2018 will be pinching pennies and building knowledge. 

My parents live in the area so if something needed to be looked at immediately, in a pinch I could get my dad to take a look. 

So if you’re not putting chocolate on the pillow and you don’t have a pond with ducks swimming in the lobby your property is not 5 Stars.

The best part about this is that now that the rest of the country is hurting just as bad, the banks are feeling the pinch corp wide and have to let these REO's go cheap.

If its going to put you in a pinch to make your payments, or having the two payments interferes with your long term financial goals or your sleep, then don't do it.