* What are the dis/advantages of ditching downtown and going outside the ring, for example to Hendricks County (besides having to start my analysis from scratch)? 

Having said that, what would be the advantages and disadvantages for me to operate under a business vs. just a personal mom-and-pop landlord?

Calculate it how you want, but the ADU COC calculation is very different than the typical COC calculation as depicted in my two examples.The garage conversion ADU also has the disadvantage of having consumed a garage.I still hold by my statement "It is my opinion that there are many investments that are likely to achieve better returns than a hands off ADU addition in most areas (there are exceptions)

I am not worried about legal fallout and disagreements, but is there any advantage / disadvantage that is glaring in regards to financing and this land contractor of having it in an LLC vs sole ownership? 

@Hong Yang if you want to do it you will have to take on the cost of due diligence and it is unlikely the seller will agree to pay for the actual inspection as it is to their disadvantage to have you do it.

I would like to understand what are the advantages and disadvantages of being a landlord with tenants from Section 8 ?

Each of these has its advantages and disadvantages, so choose one that best fits your style and strategy.3.

There are advantages and disadvantage to both long term and short term.

However, without knowing the local laws etc you are at a disadvantage.

There are advantages and disadvantages to different minimums.