In desperation, I even visited their office in person, only to have my concerns dismissed and another empty message taken.

My concern is that I might be over leveraging myself if I try pull out a 20% down payment for a DSCR loan.

Concerns: Although the cashflow is good, we weren't sure it's valuation and potential for appreciation since there is no good comp like this property in the area.

The current owner is usually not be very inclined to give the news to the tenant out of concern that the deal does not close and they have to deal with the vacancy.

Also, when it comes to these infrastructure items you are concerned about, learn more about the "options".

My main concern is not being able to cashflow the property using the LTR route.   

While he wasn’t successful getting the insurance companies to accept liability (initially), he pointed out to the plaintiffs attorney that (1) the owner of the condo was an LLC, not me personally, and that’ll business concerning the condo was done in the name of the LLC, and (2) the only asset of the Series of that LLC was the condo itself, so that the legal entity owned only that single asset.  

That was our concern with including it. 

I had similar concerns as a noob 16 years ago, what if I can't find a renter.

They are people and have needs/concerns too.