I’ve made hundreds of thousands of dollars in both retail RealEstate and Investor arbitrage RealEstate both sides of the spectrum and I can tell you that I personally know a lot of these girls and I could address this right now that they are millionaires and they know exactly what they’re doing.

I'm trying to figure out where on the spectrum I fall with risk and leverage

Buying on the low end of the price spectrum is risky.

My main barrier is:1) Lack of Cash-flow - I live in a market where rental rates and home prices are on opposite sides of the spectrum.

The questions are (1) where on this spectrum do you want to be and (2) what is the best way to get there?  

Risk is neither good or bad.Real estate on average tends towards the low end of the spectrum, but of course real estate runs the gamut of risk.

@Michael Norwoodall of the things you listed are viable options, but some of them are at opposite ends of the spectrum in terms of time and hands-on-ness. 

The last group will never ask when is it enough, they live for the hunt.At some point in that spectrum you will ask either I’m bored and want to be challenged (overseas investing) or why/ what is the purpose of my success once you get past the basics, which then is pure enjoyment.  

I have clients on both ends of the spectrum that buy cash and are very happy with their outcomes.

He's definitely on the spectrum and more or less obsessed, so he's got a great avenue to pass this to.My sons are much younger, and I'll decide what I have to do with mine but I am pretty confident they'll want this for keeps.