It seems you have a great income already and a cash flowing property in Pennsylvania, so are you comfortable with something that breaks even and is an appreciation play or are you looking at purely cash flow?

Not everyone has the time and ability to do that and not everyone feels comfortable turning over control.

Nowadays there are an abundance of platforms such as Buildium and DoorLoopWhen you get to a certain unit count, it's worth switching to Appfolio.Try to pick a solution that you can grow into and you feel comfortable with their platform

Get out of your comfort zone.

We wanted a house hack where we could live comfortably and relatively mortgage free for a few years, so we could save more to invest.

I have had friends buy a great condo and then didn't read the docs well enough to know that they limited how many units in the building could be rented out at a time.Remember that there is no right or wrong way, it just depends on what path you are most interested trying out and feel most comfortable with.

The space should accommodate your family comfortably, so if it meets your family's needs, it could be a good fit.When considering your third property, think about what works best for your family.

From a capital standpoint, I am comfortable with another down payment on a house hack on a multifamily.

I like the comfort of knowing that someone as a vested interest in holding my hand, but I'm still a little skeptical.  

Finance with a bank that's comfortable with a long-term fixed rate mortgage in the LLCs name.