Look for ways to make the home stand out - unique theming, advantageous location in the resort near the clubhouse, or with a view.

This is not worth the effort and risk of owning a duplex.

The property, though is not beach front, nor does it has ocean view, is just a short drive from some of the best beaches in the west, which are great for surfing, snorkeling, SCUBA diving.

Why PM does not inquire to bring potential tenant to view occupied property upon tenant agree?

If I were starting over, I’d go this route again without hesitation.For Milwaukee, look at Riverwest, Bay View, and West Allis as each have strong rental demand with room for appreciation.

Only the house 5 down with the same sq ft is literally worth 100K more because the neighborhood actually changes in those 5 houses. 

Well worth the commission to find a good deal or stay away from a bad one. 

If it's the difference between $1800 and $2200 but you have to cover utilities too, not worth it. 

Maintenance/cap ex, insurance, if a rental PM, bookkeeping, misc.The fact you have a loan means 1) leverage 2) equity pay down.In addition, there are tax benefits.So I will do some rough underwriting as an OO non-rental at 95% LTV (because FHA has some undesired consequences that make the 1.5% difference in LTV worth avoiding the FHA).equity paydown: 20% (using OP interest rate at 95% LTV and not counting closing costs). 

In my view, regular home insurance is really no different, and adding the Aircover makes it better than any insurance I have seen.I see that STR insurance can benefit people who can’t utilize Aircover though.