We understand that not every negative item we dispute will come off.We persist until we succeed because you must have a high-level of doggedness as a real estate entrepreneur.We understand there will be sunk costs and time being wasted.

The property taxes will be on his Schedule A during the time the property was his primary residence, assuming he itemizes.

Anyone that has sold items privately would have countered any offer. 

And addressing my item #1 comment, almost always, when a "distressed" homeowner is approached, they initially are grateful to have the loan brought current, but before long they forget the circumstances they were in and you become the bad guy that stole their house.

There are a lot of options out there.Some of the most useful items BiggerPockets members have identified are features that save time so they can spend time working on their next property.

Of course you can get discounts for having certain items FULLY updated, like plumbing.  

Paying off the notes, working to pre-emptively make repairs to capex items before they fail or become a major issue think roof, HVAC, and foundation.

I do emphasize on showing that my 1800 property is not going to magically become modern. 

The itemized damage estimate that my insurance provided me lists an Actual Cash Value that is 15% higher than my Dwelling A Coverage. 

or, do you cash flow only after you've set aside money for capex and other items?