I'm a retired engineer and have been successfully using income from these houses to support my retirement without dipping into retirement savings.I'm transitioning my business from rentals to a franchise and would consider selling one of my houses (5 br/4 ba - the other houses my son while he's still attending).

And you must use all of your proceeds ($300K ish).   

It separates your personal assets from your business, providing a safeguard if any legal issues arise related to tenants or the property.

Similarly, quality dividend-paying companies often retain some earnings to reinvest in their business, increasing the company's (and your) value over time.

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

And you get feedback at a level high enough to determine how to proceed. 

The program has been great for my own STR investments and my co-hosting business.

My motto, "Honesty, Integrity, and Accountability," has always been my guiding principle—not just in business, but in my personal life as well.

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.

It would for sure have to be a higher hourly rate than a typical W2 job however as agents are 1099 contractors and there are expenses associated with maintaining our licenses and operating our businesses that usually come out of our commissions.