This is super helpful to hear the contractor point of view. 

I have had permits in other jurisdictions be quite easy.My view is I would let someone familiar with the process do it unless you were planning on applying for many permits over time.  

We will be adding a day light basement to their Studio House plan to capture views of the lake we are building on.

We converted a old restaurant on the property to a coworking lounge, redid the pool and built out the roof to a entertainment center with fire pits, lounges, bubble chairs, barbeque, large screen TV, music, yoga mats and amazing views of the ocean and city lights.It is designed for coworking/coliving for business professionals and entrepreneurs who want to...Live where they work.

There was an offer that blew up because of a defect in a "view easement". 

Depends on how you view risk and how stable your life/income/etc are for you.Assuming all of that is stable, I'm buying properties for sure. 

Certain expenses are all lumped together for the sake of the P&L like insurance and taxes and others like repairs and maintenance can be viewed collectively or by individual property.

We keep seeing conflicting views but my personal experience with buyers indicates that the outlook is positive.   

How might a city board view a project such as this and what might be some of the bigger questions they would ask of us?

Here’s how brokers typically view these:Loan Term Sheet vs.