Meanwhile, in the 4 years in limbo massive redevelopment was occurring in the area, and we were offered an amount equal to our investment plus a reasonable profit by a developer.   

I was agreeing about your comment as to having a mentor, then I realized I didn't have a mentor when I started.Brandon, there were books, I skimmed the "Paper Game" don't recall the author but it was conceptual and a little too fluffy for me, I didn't really start by using anything in that book, if I did, it was by accident.

I wouldn't remove auto-pay on your utilities from your credit/debit card if you have them, don't want to miss your electric bill by accident but any daily/casual/somewhat necessary spending is cash.

There is no demand at-all for these properties.So in a worst case scenario as you state, the amount of money to be lost may be smaller, but it has a much higher probability of occurring than say a California property not appreciating over time.  

Here’s what I do with my rentals:I either have tenants split the utility bills or include a clause in the lease that states if the gas or water bill exceeds a specific amount ($X), the tenant will be responsible for the overage, provided there are no leaks or other infrastructure issues contributing to the high usage.To determine this $X amount:Water: I take the highest water bill I’ve had over the past year (excluding periods where leaks occurred) and add about $15 to account for small fluctuations or potential increases.Gas: For gas, I calculate the median bill during the winter (when usage is highest) and the median bill in the summer (when usage is typically lowest).

The equivalent tools to Priceline have been in place for the transition you describe to have occurred 20 years ago.

It feels like everyone and their grandma is on the Do Not Call list nowadays and my worry is the fines associated with accidently calling these individuals. 

One, the investment may have been one that worked well but a mostly unforeseen occurance happened, to either the economy in general or to the subject investment in particular.  

I’m aware of loss harvesting when it comes to stocks, bonds, etf’s, etc. but how can this occur with real estate?

Capex- how much capex is needed, and what happens if only xx% occurs?