And what's the best next step if want to assess the situation?

Even after being licensed I bought and still by dozens of homes per year through other agents if they bring me deals.

In terms of appreciation, what makes the deal tough to pass (if I get it of course) is that the last assessment came in at 210k (2016) and I am hoping to get between 160-175.

This will allow the Hard Money Lender to assess the current as-is value of the property.You should also provide your Fix & Flip Comparable Market Analysis supporting your proposed After Repair Value (ARV).

A turnkey company may have a dozen properties for sale and in the same city there might be several hundred/thousands for sale on the mls. 

I have a need for an assessment from a Structural Engineer for one of my properties.

They said it happens more than you think, (typically when logging or clearing land), and there were three ways to calculate the replacement value of the tree: First, what is the cost of buying a 20+ year old tree, transporting it and planting it in the same spot; Second, have a property assessment done showing the approximate loss to the property value based on the percentage of landscaping destroyed; Lastly, have an arborist come out and do a calculation where they "rebuild" the trunk based on the cost of a smaller tree of the same species.I went with the 3rd, as the other two just seemed unreasonably high.

You should also ask for meeting minutes, as these provide additional insights into the operations, pending assessments, violations, landlord/tennant issues, etc

Buy simple and cheap, you can always treat yourself to a much nicer home 5-10 years from now once you already have a dozen other income generating properties and are financially secure. 

I was actually using this listing as an example, I agree with your assessment about Hampden.