Save your money and build a  network of realtors , real estate investors and  go to meetups

However, it is hard to gauge the rental potential so many years into the future with new construction SFH and apartments being built in the next few years.I’m worried about the HOA, the rental potential, whether I should keep saving and buy a SFH, or if I should just take the plunge and start building equity.

I'm going to assume the obvious that it is tied to a home, land, commercial building, etc.?

I'm looking into the Credit Stacking program that Jack McColl runs. Looking for any reviews from previous students. 
It's a program that helps/teaches you how to access business credit to fund your business endeavors...

I have personally been raked over the coals on some south side properties with squatters because I wasn't prepared for the time it would take to stabalize the building.

Likely it's that they legally have to have a physical address and as they meet clients at clients home, have them pick out roofing in a catalog and have it delivered directly to the client, there's no need for a physical building.

I have bought and sold six homes, had one beautiful flip, and kept one duplex that was a BRRR score and currently building two more duplexes with the opportunity for one more that is build ready.  

I'm considering purchasing a commercial office building that has 4 suites. 

More interestingly, a current tenant has a direct relationship with the owner and is close friends with my Client.

A generalist is interested in many asset classes and strategies, making it impossible to focus.The best way to steer clear of analysis paralysis is to research, build relationships, and get the confidence to make a first choice regarding your intended asset class.