I watched as people purchased lottery tickets by the dozens.

I agree with your assessment that the numbers have to work after you move out, but you can compute that on your own using Rental Property Calculators here on BP. 

It know thatTo me that sounds very strangeI own Two houses on the same street both assessed the same amount.  

Here's my general start to assess a deal. 1.

We don't start in the morning and go grab materials at home depot in the afternoon, we have materials delivered and we pay delivery fee, client eat that bill to give way to our convenience, two dozens of 40-70/trip could be avoided but we rather spend time making the 1-2 hour trip to the supply store and work on our clients project, we know 2 hours of manpower is much more expensive than $40-70.

There are DOZENS!!

A lot of cities are re-assessing the values in high market areas the the amount assigned to land vs. building is getting put much more toward land- because ultimately that's what's going up in value more.

I find it very easy to challenge our assessment.

They probably have a dozen layers of paint! 

What you're pointing out aligns with my initial assessment and calculations.