From day 1 you should be mentally prepared to go into debt, and set yourself up for success in that regard.

It'd also be great to take a mental break from sitting and working in information security all day; I swear I'm losing my mind from all of these alerts...

You place zero value on cash, this makes you simply a speculator on this property and probably most of your properties all have zero/negative cash flow for the same reason (excluding possibly your low end investments).You would be way farther ahead to pull the cash, park it in a mutual fund and and reduce your losses on the property if you really want to hold on to it.Obviously having a cash hording mentality driving you to pay off properties/mortgages this will never work for you, understandable but not investor wise.

BUT I've also contacted listing agents before and just never heard back, I assume due to the same mentality Russell described above. 

I think we are just so used to getting no said to us and our egos crushed through all of our training that it gives us the mentality to push or find creative solutions when others will give up. 

There were a number of factors that led to doing it at this point:1) The time it took to maintain both my day job and manage the portfolio was taking its toll2) I was making more money at a lower tax rate with real estate than the W-2 income3) I was mentally ready to focus on real estate and change my quality of lifeYou are definitely asking the right questions and as someone who had the same goal and has not made that goal a reality, I'm rooting for your success! 

I think it was the mentality of the area. 

You have to be fully committed and mentally prepared to take on any investment but even more so in a situation like this.You can get the addresses of absentee owners for free on the county tax website but you just have to do the legwork to turn it into a list to mail to.

We'd be happy to continue this model, but the new x-factor is my aging parents will soon no longer be mentally capable of signing legal docs.  

You have to mentally accept, if you go this route, if you want a deal, you are likely looking at renovating.If I were in your shoes, I'd take myself mentally out of the equation, and look at the numbers-- where can I buy a house, or a multi-family house and make the most?