Can someone come to a mutual understanding of the idea that I'm trying to express about having multiple or as many ways to buy property?

Someone eventually talked him into investing in a syndication and he realized he was making a great return without any of the effort, so he invested in more.

They could use the tax break for gifting into someone's 529 and I wouldn't claim the money that goes straight into the kids 529. 

You would then end up spending time cleaning it once they've moved out, or would hire someone to clean it. 

And to my point, once the rules specifically disallowed the transaction THEN it was disallowed.The risk to someone contemplating an MIS transaction is that the IRS find that it violates some existing statute or rule, not a future ruling.This is what tax attorneys do.

Not sure if the answer isa) nothing I can do about it, b) put a wireless water meter to help detect leaks on it (how does this work for a rental where the internet is theirs?)

You're just taking money away from your business when you use it personally, and in that case, you may as well not own it, and rent someone else's because 1.

@Josh Mac keep in mind that Zillow can be completely unaware of factors that affect value...and some of these factors might not be apparent until you see the property in-person.For instance, maybe someone added a bathroom to the house, and now it's a 3/3, but Zillow thinks it's a 3/2.  ...or maybe the house is right next to a busy road with tons of traffic noise, but the Zestimate is based on nearby houses that are on quieter residential streets  ...or the main floor beam under the house is rotted out--Zillow would never know that...In short, there are a ton of factors that can affect a property's value that Zillow might completely miss.The Zestimate can be reasonably accurate in showing a ballpark value...but, I wouldn't make life and death investing decisions based on a Zestimate...

Any tips for someone starting out that you wish you knew?

I'm not sure how this setup would be received by someone wanting to build a home.