A good CPA, advisor /planner, attorney, and self directed custodian can all play a distinct role for the items you identified.

Hard Money Lenders also promote themselves as Private Lenders as well, but there is a distinction.  

Members of the family that purchased the home say they would like to remain anonymous, but admit they’re big fans of the house’s distinctive mid-century modern architecture.

This was a clearly mapped property here in CA, when you get back east to older deed subdivisions the issues can be even more distinct.

The cash flow vs appreciation is an important distinction I didn’t think of.

There is a distinction and a decision you'll need to make.

I understand starting with distinct criteria to start your investment journey, but wondering what it took for that to change (if it ever did).

Your response led me to Googling the difference between NWROI (Net Worth Return on Investment) and Cash on cash and it yielded the following distinction: "Cash on cash return measures how much cash an investment property will actually generate, whereas ROI measures total wealth buildup"So my takeaway is maintaining a positive cash on cash return over prioritizing concern for ROI in order to accrue enough funds to put a down payment on a non-FHA loan for the second property

I know this is an older thread, but I wanted to chime in.Assuming we're all talking about contracted cleaning companies (no employer-employee relationship, in which chase employment law may come into play), I think a distinction needs to be made between terminating a contractual relationship as a course of business and firing a contractor for cause.Terminating a contractual relationship when there's no malice--just a desire to change contractors to someone who will fit your needs better--is rarely an emotionally charged event.

Dion DePaoli, this brings up an interesting distinction.