I think the flip side is that there are many on their deathbed who realize they have no idea how their family is going to eat a week from now....and perhaps said family watching the breadwinner die are realizing it too, or they will realize it soon when the bills start coming in...

Plus, your initial expenses due to deferred maintenance will eat into most, if not all, of that. 

I like to have my cake and eat it too, so I’ll keep researching.

My guess is you have a car payment and eat out a lot? 

First few years, depreciation will eat most of your income so you might have very little to actual tax savings from the rentals.If you dont have a w-2 job, your rental income determines your income tax bracket.

I can eat a $10k-$20k unforeseen expense (Contamination, burst pipes; etc etc) when my profit is $100k+.

Because of this, I'm missing out on good opportunities because somebody else is eating me to the punch.

Nice cars, big house, sweet monthly vacations, eating anywhere and everywhere I want (#singlelife)then after that I'm all about just paying for more time with family, future kids education, health, relaxing. 

I guess I'm curious what your own threshold is before you say as the property owner "just replace the damn thing, eat the upfront cost, and stop sending someone out there to unclog the sink."

The fines will eat up at their profits.