I was conducting an extremely seasonal business and after 8 years of operation the business was insolvent. 

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

Business leaders can’t stop talking about this “pro-business administration” that is coming on January 20th.

I contribute that much monthly any way as my side business helps to get me where I want when I retire. 

Which would be more effective for pitching my Airbnb arbitrage business?

Median household income can be an indication of the area.It's not feasible to manage D-class remotely or with 3rd party management and make a profit.

I have two phones, one for business and one for personal.

Here is what the IRS says on the subject: Election for Husband and Wife Unincorporated Businesses A business owned and operated by the spouses through a limited liability company does not qualify for the election Only businesses that are owned and operated by spouses as co-owners (and not in the name of a state law entity) qualify for the election.

We made a lot of mistakes like working in the wrong order and doing work just to keep my employees busy.

Usually most franchise models in other business environments have the whole package.