I am thinking of ways to start getting comfortable analyzing deals and assessing ARV. 

I have a few chimney repair people coming in the next 2 weeks to assess the damages and help determine the cause but was hoping for some initial opinions as it's taking a few days before anyone can come out.

I also found out that the back taxes were inflated by about $1,750 due to an environmental assessment that had been added but never completed.

Reserves are more of a personal assessment of the level of risk you can afford to take.

1) Is a property reassessed on every sale to a new market value or does it maintain the previous assessed value? 

@O'Neil MbakweYou are confusing the tax 'Assessment" with the word "Appraisal".

So you are really assessing the risks of the sponsor up front, and project as it comes through.

In one town near me property taxes are a full percent of assessed value higher than other towns, even in the same county.

Go online and see if you can find the tax assessment card for the property; you can typically Google 'Town Name + GIS", you should get links to the town GIS site. 

I like the low rise buildings (no elevator) they tend to have lower assessments and more rental friendly.