I think I am a bit technologically challenged, so trying to see what are best options if any. 

. - which I suspect you're already inclined to do.You can also investigate various methods of pipe replacement / renewal that involve trenchless technologies, such as pipe lining, pipe bursting, or directional drilling.

If you are NOT running a trade or business - 1099s are not required.The main reason why you WANT to be "running a rental trade or business" is your eligibility to claim business overhead deductions, such as marketing, education, technology, and so on.

We self manage from Chicago and it’s very manageable in this market with the help of today’s technology.  

The technology is getting better, cheaper and thinner.

My take as an insider is that it's because it's actually a much harder job than many might realize, and a consultative/ interpersonal/ hands on one that simply cannot be replaced easily with technology. 

"This is a once in a lifetime opportunity to capitalize on the new "industrial revolution" of the universe changing technology that AI is""Join now or miss out on our artificially intelligent, augmented reality, virtually based, digitally integrated and blockchain based revolutionary technology""This is the next NVIDIA" - John McAfee

This technology is very interesting IMO.  

Padsplit is simply a technology platform.

These I think are considered rookie mistakes, but I'm all about finding ways to reduce risks from human error.Has anyone else considered technological solutions to help the due diligence process?