Put another way, I am less concerned with cash flow in the super near term but rather looking to make investments into solid rentals that will produce sufficient cash in 5 years.

This produces 10% cash on cash, which is on the low end, but you have no management costs in the expenses. 

Otherwise, you can get duplex/tri/4 plex in Minneapolis that produces decent rent/price, but definitely not for 1m. 

The other months I will be back home producing wine.

In hopes those cash flow and produce appreciation to then leverage.I am leaning toward buying a 100 - 120K property, which would wipe out my emergency funds.

Purchase price: $420,000 Cash invested: $25,000 Income Producing Conforming Triplex in Fort Lauderdale.

Make sure that the mechanical closet is vented to the outside if anything in the closet produces CO2, put in a closet, have either 2 doors or a door and window that is large enough for escape in case of a fire. 

I would start by researching top producing agents in the area and reaching out.

One bad tenant could eat up two years of profit without even trying.If you have $70k in equity, I would seriously consider selling the condo and buy a multi-family that produces a better return.

Fast forward 3 years, I have 2 new roommates each paying me 750 for a room, and a tenant downstairs paying 1300 a month producing an AWESOME cash flow.