Are they paying market rent, are they excessively long or about to expire, etc etc. 

@Cj PowderhornHi CJ, Regarding your Cape Coral experience, the median time on market for duplex rentals for the April to present time period was 37 days, so yes, your vacancy period for that unit was excessive.

It will typically last long enough that it goes out of style before it needs replacing from excess damage.  

Depending on your interest rates you may be able to get a better return on your excess money than by paying off the mortgages.

Speaking as both an investor and realtor based in FtL, these small MF are very difficult to get into at the moment due to excessively high pricing leading to negative cashflow if you plan to finance them. 

I understand where you're coming from, but to throw fuel on the fire, Brandon Turner turned 30 last year...

Find your motivation for your goals and use it as fuel to work toward them every single day until you reach them and surpass them.

As a Property Manager in a market where many owners choose to manage on their own, I've seen several examples of owners losing their homes or properties because their tenants did not pay or caused excess damage.

When you buy a property, and hold a mortgage on that purchase, the excess cash you have between rents and costs is a form of profit but the short fall is NOT a loss, it's additional capital investment. 

While that bodes well for opportunities, the out of pocket cost would be excessively high as well.