Many times, a listing agent will use estimated rents for vacant units and those estimates might be for full rehabbed modern units where the existing unit is not near that.

If you're analyzing a property and the roof, HVAC, furnace, and water heater are all past their life expectancies, then plan to account for these items in your analysis and increase your CapEx.

Plenty never like to finish the punch list. 

You should check for your state's exact laws if it is one of the many listed in the article.  

I’m concerned if I say enough like town or price listed, arv..they can cut me out and go right to seller/ agent.

@Jonathan R McLaughlinyes some big ticket items here. 

Cincinnati and many of the surrounding inner ring suburbs can be very street by street.As for STR, unless you have something fairly special and are great at marketing your property beyond just listing it on Airbnb, you will likely not have a homerun deal.  

If I am able to make tax deductions or write offs from repairs/ maintenance items how can I do so?

If the seller is worried their house will go back to market - they would have to fix or disclose these items anyway.

I have spoken with Quicken developers @ Intuit and they know about couple issues we found, but it is not on their top of the list.