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

." - Exactly it's a business and there's little grey area when PM is done correctly. 

house hacking is great start, that's how i started in the business. would love to connect

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). 

Quote from @Chris Magistrado:The point he's making is that the agent must take responsibility for building and maintaining their business, and the Broker won't play much of a role.

My only reply here is to say to simply focus on the business objectives.

I inherited a partnership in a 22 unit commercial building with 8 restaurants, a grocery store, a couple of personal care services, and various other businesses.

Looking for some guidance on resources of how to begin analysis or how to build a business of this sort.

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

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.