Calculate your current ROE and assess it relative to other investment opportunities.ROE = (cash flow + mortgage principal pay down + appreciation) / (value - current debt)

Insurance companies have any begun to charge more for Philly row homes, and the property assessment continues to increase year after year. 

But just recently the city of Milwaukee did an annual assessment of that property and went up 30k in value. 

Plus you have to deal with HOA restrictions, possible special assessments, etc.

The town now has it assessed for $1.1M which he fought the whole way through the process as he is a lawyer and knows the system and can do it himself for free and has gotten no tax relief.

They're just going to give you their honest assessment of the community. , the other thing I often do when I'm starting to evaluate a new market, I subscribe to the local newspaper or the local business journal and doesn't cost that much, usually $5 to $10 a month.

Something that cuts through the noise and provides me with the essential metrics necessary to assess the quality of a potential investment quickly and efficiently.I'm open to suggestions and advice from those who have navigated similar paths.

Its hard to make broad appreciation vs cash flow assessments without looking at the individuals goals and situation. 

What do you do to assess properties and make informed investment decisions?

I usually say something like, “we encourage future potential guests to read all other guest reviews of our property for an honest assessment of what to expect.”