In my opinion it is the best way to learn the ropes of management and operations while de-risking things quite a bit (you're there every day). 

I live in Newark Delaware and work for a financial institution as a Vice President.

Quote from @Kelly Monteiro: @Susan Walsh, where did you see the $ 100K limit, I've been researching on this bill and haven't seen anything mentioning that, not sure if it changed since your message was sent.CHAPTER 235504 (c)(2)(A) For purposes of this subdivision, a short-term rental facilitator is considered to have de minimis facilitations of short-term rentals if the facilitator derived less than one hundred thousand dollars ($100,000) from facilitating short-term rentals during the previous calendar year.

It's around 4 acres of land that could be developed into a cul de sac with ~10 SF homes.However the lot currently hosts a 5k sqft commercial/industrial structure (made out of metal). 

Through my marketing I have been getting more deals in Delaware County, PA.  

Thank you, Appreciate the callout @Paul De Luca!

Our concern with this is that our current primary is across from the best school in our area on a cul-de-sac lot and we feel it will continue to grow at a high rate and don’t want to miss out on that. 

@Ramiro De Leon Welcome to BP and great choice on looking in Denver!

I'm not too clear on whether I should set up a holding company, (Delaware, Wyoming, etc). 

Just a note- I confronted them with their suspended license multiple times and the squirrely agents sent me a new business license that they have in -  I believe Delaware?