I am not originally from here, so I keep an objective view of the overall city and the real estate market as I'm not really emotionally tied to an area.

It depends on what your objective is and whether you're  willing to invest out of state.

Start by defining your goals and objectives and then evaluate markets based on their ability to achieve those goals.

What options are there if you have objective data to support a reconsideration of the value? 

With a legal 2 family, you could eventually move out of the unit and add a renter without any objection from the municipality. 

Maybe compensate him well for his time so he can give you an objective estimate and not feel like he needs to downplay the repair costs so you'll be more likely to buy it and it's not a waste of his time.

Don't pay 10k cc or even 5k.I chased the shiny object of a 30yr fixed rate for years.

Most objections come to the offer pricing. 

The same probate court has accepted my filings in objection, but everything is backed up right now and there are many burdensome factors in play. 

Below is a draft of the workflow:Main objective: Improve our ability to analyze a dealGeneral rules and info:1.