Or is it unavoidable and am I just hedging on multiple properties not becoming vacant simultaneously? 

Since I cannot find a clear answer to this - am I correct that IRA distributions count as ordinary (taxable) income and therefore we can use up to 25K per year of the passive carry over loss to reduce the tax liability incurred from the IRA distributions by that 25K amount?

Am I understanding that they offered to take care of the painting? 

Am I required to hire a professional to inspect anything/everything. 

Because you sometimes get the procrastinators and boundary pushers who will start acting like the end of the grace period is the real due date, so if they're only a "day or two" late from THAT, why am I making such a big deal. 

So am I at risk of a repeat situation here?

Well, how am I going to sift through the millions of people on social media to target those that may want to sell a house right?

Hi @Sam Johnson, just my 2 cents here and by no means am I an insurance expert.  

I agree look at it as what percent return am I getting on equity.

If I have to, then what sort of costs / fees/ expenses am I looking at?