I will be quick to admit I have only had experiences with small rentals (6 units and smaller) so if you are looking for help on larger apartment complexes I would not be a great resource.

On property number one, I would cash flow $750 a month after mortgage, taxes, and insurance if I also rent out the unit I live in.

You may also want to look into 2-4 units as those are the easiest to finance and help you grow faster.

Duplex have different zoning that may permit additional units.

Here is the scenerio:3-unit investment property worth $2m.

House hacking is using an owner occupant loan to get into a home or a 2-4 unit property.

I am currently in the market to purchase a tri-plex with the plan to live in one unit, make upgrades, and rent the other two out.

I am renting two units (1 basement and 1 side unit) in my primary residence.

Then, how does that look if you were to updated units and move out and rent both sides? 

That insurance lesson is gold, props to you for keeping perspective and having a solid team to help you navigate through it.