@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

It does sound to me that a lot of that work should have come out of the tenants security deposit 

If yu claim one it doesn't void the option to claim the other one.Provided you meet the IRS requirements for both, as a tax strategy, you could complete exclude a portion of capital gains under Section 121 and then defer the remaining capital gains under Section 1031 (@Dave Foster is a great resource for 1031 exchange). ..

After thirty years of flipping houses I can tell you that the second you trust the subs completely, things go wrong.

I doubt it would qualify for a conventional loan with the repairs that need to be completed.

Second, in terms of asset protection, LLCs are not invincible, but I think what many don’t understand is that they are not designed to completely shield your assets from liabilities, on the contrary they are designed to contain and isolate liabilities.

In your case, it sounds like depreciation would give you a lot of benefit even without qualifying as REPS.As you mentioned, the kids will get a step up in basis when they inherit the property. 

Sounds like a good deal, congrats Scott!

So I can completely surrender the homeowners insurance right? 

I think they contain solid information and will help lay a good foundation as a beginner (Haha, I'm completely new to real estate as well, btw)I'm also going to be reading the following books, and hopefully I can finish all by the end of this month:1) The ABCs of Property Management2) The Advanced Guide to Real Estate Investing3) Long-Distance Real Estate Investing How to Buy, Rehab, and Manage Out-of-State Rental Properties (this might be the most important one to me personally)4) The Book on Investing in Real Estate with No (and Low) Money DownIn addition to reading, I'm consuming crazy amounts of youtube videos, and I'recommend you do this as well.