3) Am I crazy to try and get back into this line of work while leaving a near six figure income job that pays the bills but does not stimulate me?

The problem I am encountering (with every field of law) is that they don't seem stimulating, especially after the other kinds of work I have done.

Another caveat is the Town gave tax abatements to new construction homes (no taxes for them) in order to stimulate some growth to the area. 

I didn't read all of your lengthy post directed toward Bob but I know that @Bob Floss II is a very sharp attorney and investor and his post was thoughtful and meant to stimulate conversation.From what I did read of your posts, our differences seem to be more a matter of opinion as opposed to fact.

Which stimulated growth in all areas. 

Doing whatever I find stimulating until I don’t find it stimulating anymore... then finding something new.

Or better yet, there are countries that do not tax capital gains at all;  as this stimulates the economy and encourages investment. 

Opportunity Zones - Jobs act of 2017 has stimulated growth by offering tax incentives in special zones around the United States2.

I just wrote a BP blog post with this title but I thought I'd lay out the main ideas to stimulate further discussion.

Finding exciting "work" is fulfilling and rewarding, and keeps us mentally young and stimulated.