I currently own two single family properties in Milwaukee.

Because you have the potential to move around a bunch, it would be worth looking to find a small multi-family property where you can live in one unit and rent the others.

No live in Pennsylvania.thank you Have the family clear out the unit.

I worked for a group of real estate investors when i lived in Phoenix Arizona for about 3 years before having to move closer to my family here in Columbia, SC.

Buying a single family home first or buying a duplex?

It depends on how much capital you have but I recommend either house hacking (3.5% - 5% down) a 2-4 unit property or you'll need 20-25% down for a non-owner occupant purchase which comes with higher rates.I would say house hacking is not an option for me, because I have a family with 2 kids (need good schools). 

"I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.

I am trying to raise money from Friends and Family for putting together the down payment needs.

Someone smart enough with enough influence to get the family to sell.

Do you know how much it would cost to find land and build a 2-4 family there?