I live in Miami Florida and I pay over $3 per square foot in rent with some going as high as $5.

That could mean working with an investor willing to fund the deal for a share of the profits or starting smaller with a house hack or live-in flip to build credibility, or putting sweat equity into a deal with a partner to learn and build your track record.

She's from CT, but lives in CR for most of the year, so I assume she'll know some local folks.

Condo ownership provides clear property rights but means living under HOA rules.

You will likely have negative initial cash flow reducing this return, but typically the negative cash flow is short lived. 

This 4 Bedroom, 2 Full Bath Home Features Almost 1,700 Sq Ft of Living Space.

I was working through the HELOC process since we have quite a lot of equity when I suddenly got denied because 1 of the 5 units is owned by someone who lives overseas and rents out his unit.

We would buy a house live in it for 2-3 years then on to the next and rent the old one out.

Most maintenance won't pop up in the inspection report, its more apt to pop up after having someone live in the property for the first month.    

I live in the Champaign area.