Let's set aside COVID influence for now and assume that the market was still good, how do I know when to diversify to a different market if at all?

I have a young person who I am desperately trying to influence to do something material with his military signing bonuses.

He knew about business, legal issues, tax issues, marketing, sales, promotion, networking, and most importantly he knew about people (psychology).The first thing he did was tell me that I have two ears and one mouth, and I should listen more than I talk.Second thing he did was have me read "How to Win Friends and Influence People" by Dale Carnegie.Then he taught me how to set appointments was home sellers, go out to their home, and write up a letter of intent to purchase or lease.He said to me, "your job is to bring me potential home sellers will consider a creative offer."

I have found Dave Ramsey's teachings to be really really valuable and he has influenced our conservative approach to RE investing.

Other than REIA's and your sphere of influence, how do you find and connect with Private Lenders?  

Zillow, Realtor.com, etc)- Call your sphere of influence.

The risk factors essentially establish an almost worst-case scenario that influences cash flow. 

Sales/cold-calling experience, customer service experience, large database of people in your sphere of influence, etc. 

You have more influence in what happens next than you think you do. 

I have been doing a lot of research, learning and listening to learn about real estate investing in the past few years and it seems to me that your first property can really influence how quickly or slowly you could scale your business.