From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

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

Try and join a few local Facebook pages and connect with locals who are in the house hacking business. 

His whole business is build to rent.

I am learning a lot about the business that, had I not gone through this process, I wouldn’t have learned nearly as much.

Holding company typically if you have multiple companies like a property manager, own property and other businesses. you will end up spending more per year on accounting and state stuff than what you make on your rentals. 

Type Line Item Fee Fixed Fee Collected Rents 10% of All Collected Rents New Tenant Search & Onboarding $600 Variable Fees Business Hour Service Calls $90/hour + Materials Cost + Tax After Hour Service Calls $120/hour + Materials Cost + Tax 3rd Party Coordination HVAC Cleaning & InspectionGutter CleaningSpring/Fall Exterior CleanupSeasonal Mowing & Weed TrimmingSeasonal Snow PlowingGeneral Contractor Negotiated Vendor Cost + 10% Oversight Fee  

If you are using STR, REPS, or self rental with material participation to convert to active or nonpassive income, you do not have to do this if you have passive business invesment that produce passive income that will exceed the loss generated by depreciation.

Incredibly poor business deal. 

Are you open to working with contractors, or do you stick with established businesses only?