Completely agree that I need to change my mindset and thinking when approaching situations!   

If cashflow is the right approach to take, what are your thoughts on the best cashflow markets?

I have strong data analytics skills and built a PowerBI dashboard to analyze the data.I was hoping to monetize this skill set by creating a newsletter and posting data insights regarding the Metro area.Is this legal/illegal/unclear?

I.e. red light=needs my attention in the next 90 days, yellow light=needs my attention in the next 6 months, green light=does not need my attention in less than 12 months.The scale can be personalized to your own needs, obviously, but it's a decent way to organized your phased-approach to a big project. 

This also works with non-clients: vendors, realtors, etc.SEO Marketing:  A long term approach is building a website that is effective and can rank well on Google. 

the "frankenstein" approach to having the loan in your personal name to me is "bad." 

How should I approach this matter?

There are tons of resources and different approaches here.

If I followed the pathway  you’re suggesting (basically if I wouldn’t start anything because I had a fear of failure) I wouldn’t have my paid off properties and I would not have a portfolio of rentals...Gotcha.I'm a little different in my approach. 

It sounds like the easiest approach is to just pay down a credit card a little bit to push it up a point.Best of luck!