@JD Martin(I wish I could quote your post above, but when I do that the UI always messes with the formatting and it gets difficult to distinguish what the quoted user said and my responses to it.)1.

But even then, Gates is distinguishable on its face from the facts in your OP. 

Group 2 is a valuable resource for you because they might be able to make recommendations for good sponsors to invest with and bad ones to avoid.I think where your question lies is in distinguishing groups 3 & 4. 

So, when you start doing business and a third party can't distinguish between you and your/the entity, its your "alter-ego." 

I also understand/respect the need to market oneself/one’s services to make a living.

Distinguish between good debt which earns you more than it costs each month and bad debt, such as credit card debt that sucks your life away. 

I would ask oneself who are you reaching out to?

When it comes to "numbers," you should distinguish between bookkeeping, accounting, and tax prep/planning activities.  

Any potential PM should also be able to distinguish between a necessary repair vs. something cosmetic that the tenant is asking for.

But not taking oneself too seriously—we love it!