Its great that you trust your realtor and the video thing helps a lot but when a problem occurs you will tell yourself "I should have went to property".   

Obviously, the risk is that at some point we might have to demo the addition if we move forward like that... curious to know if we don't invite the sort of scrutiny that permitting and passing inspections causes -- what the likelihood is of the worst-case scenario occurring? 

If tenant fails to immediately notify landlord of the need for repair or maintenance, and additional damage occurs to the premises which could have been prevented if landlord had been able to make prompt repairs, tenant shall be responsible for the cost of repairing the additional damage even if the original damage was not tenants fault.Would this be a situation where the tenant should pay for all/some of the dry wall needing replacement ?

However, in the long term, I am confident of continued appreciation in my market as this has been the case for over 60 years.I think people who think that existing cash flow is a certainty are not looking at what has occurred in the recent past (I know the impact of the GR was market specific but the next downturn may impact different markets than the GR).

@Evan Loader the LLC filing with the SEC may occur just after closing.

They also share in the loss if that occurs and you do not owe them if property goes down.

Convenetional lenders often will not refinance until a certain seasoning peroid has occurred, 6 months - a year.

@Evans Murray very sorry that this has occurred. 

Under Section 1031, once the sale of a property occurs a qualified intermediary must receive the cash from the sale (a critical fiduciary duty), similar to an escrow arrangement.

while I am not a fan of turn key, (no upside till appreciation occurs) be sure to pick an area with good rent to value, as well as durability of rents, if you are in Chicago, consider Milwaukee and surrounding, Brew City REI on Facebook is a great group, with lots of Property managers and contractors, you need to learn the neighborhoods though.