Having a long-term rental while living abroad is do-able.Flipping houses while abroad, in my opinion, more difficult, especially if its your first go around with real estate.I would recommend taking a flight and staying in the area for a week and inspect the neighborhoods and make connections.You can reach out to @Elenis Camargo who has a PM company in Jacksonville.Best of luck though.

If I put all of my eggs in one basket (Florida in this case), paid off property and a hurricane blows everything away, FEMA is nowhere to be found and the insurance companies take years to pay what little claims they actually do pay, I suffer through it in a blown out house.

Next question.... will you self-manage it, or turn it over to a professional management company, or some type of hybrid? 

What other company offers business income loss and up to 15k for dealing with squatters?

Not affiliated with either company** 

By 2030, we want to have grown a portfolio of over 100 units, created a property management company that manages an additional 100-200 units, and, finally (and most importantly), we will have established a non-profit that is focused on quality, affordable housing that specializes in providing housing and resources at/on the "services cliff" alongside financial counseling and first-time home buyer education in our target area.Our target area is the Springfield, MA and Hartford, CT areas with dreams to expand to Central Massachusetts (Worcester, MA), Southern New Hampshire (Nashua, NH), and Southern Connecticut (New Haven, CT).Would love to meet up with likeminded individuals in our area!

With that being said, in a worst case scenario, you can always hire a property management company to handle the day to day items if it comes to that. 

Of course, I run a cost segregation company BUT I would recommend that regardless.

HELOCs are not available because they are residential loans guaranteed by individuals and what you seek is a type of commercial loan or credit line which are available to seasoned companies with proven financial track record.

The substitute of collateral was more of a scenario where you sold for $155K, and instead of paying off the $88K loan in your scenario, those funds stayed at the title company and were used on a cash purchase happening nearby in date.