Coquina Key appears to check all the boxes for me.

It appears this RE has 2 of the 3 (below market and forced appreciation).  

I know it was a pain the first time, but after the first one, they get significantly easier. 

When you stand back and look at the brick house it will appear all the bricks are laid down lengthwise and you notice the rectangular sides of the brick.

Way easier and cheaper.

Although, I have turned the property I am currently living in (I own) into a duplex which would allow me to rent and move out into another to have as primary residence. will this make things easier?

My reasoning behind condo's initially was pretty simple - I thought they would be easiest to manage while learning the ropes of REI and it appeared to me that a lot of the SFH in my area were sitting vacant for quite a while (plus they wouldn't cash flow).

@Nabil Suleiman  As this would be my first property, I feel that buying local would be easier for me to manage and learn from. 

You can learn, file, pay fees, get rejected, re-apply as many times as you want.Just because it doesn't appear complicated, doesn't mean its easy.

The "community" consists primarily of townhouses and appears well maintained.