The STR, if purely an appreciation play,  is speculation to me. 

Most gulf front investments are mostly appreciation plays unless you do a serious renovation.

It's good to hear that you want to play the long-term hold game as that is how you'll ultimately build equity.  

I negotiated this property by trading my owned property for this one, as it was a brand new property in an area being developed.

If you stick to American name brand units that are basic - no fancy sensors, doodads or anything else - W/Ds are surprisingly durable, even with renters.

If you're aiming for growth and can secure a low-interest mortgage, financing might be the better play.

There's a high chance that you are feeling FOMO from the returns in public markets, sell your houses for a loss, pile into stocks, and then see mediocre performance while real estate heads back higher again.I see this, and similar actions, play out over and over.Personally, I'd stick with the real estate rather than selling it.

I have a contrary play. 

I personally would always play the role of GC myself.

I pay 4000 a year in taxes for a brand new single family home I can only collect 1100 a month on....4 months of rent to just cover property taxes,  insurance is another 4000k.... that's 8 months gone.