If your occupancy rate drops, you may able to patch the damage by trying other platforms but this will further decrease your ranking on the system in the future. 

If this is how a cash out refinance works, it feels like the strategy is to either have more to rent out within the property (multi-family), wait for average rents in market to increase, rehab the property more and increase rent more, pay off the property/ more of the mortgage and refinance again without a cash out to decrease the mortgage (I don't even know if I can refinance a property twice)? 

To decrease the amount of money you pay out of pocket you could turn part of the home to a STR or MTR.

I can't remember, but it turned out that since I kept paying my broker 1%+ every time I re-financed my principal never decreased.

early/prepayment only decreases the income/value of the pkg. 

decreasing appreciation?  

How do you evaluate the increase (or decrease) in price of the land in question down the road?

Unfortunately, not only is the Orlando property losing money every month, but it has also decreased in value since I purchased it.

I have added pre-payment penalties on my refinance loans to decrease my rate substantially. 

If an asset is throwing off a certain yield that is not commiserate with it's risk, then investors will then begin paying more for that asset, thus decreasing it's yield....or start paying less for the asset which would increase it's yield, until it was at the proper risk/return rate to produce the yield that is truly reflective of it's risk.The problem is novice real estate investors get the risk/reward correlation backwards.