You are encouraged to timeblock 3 or 4 hours a day to cold-calling and lead generating activities.

Before I answer your question (as best I can), know that I believe you should only buy properties that generate a sustained positive cash flow and are located in an area likely to appreciate over time.

I would assume this is something that can be generated on MLS.

Since I would only be using licensed, bonded & insured contractors, I would be more concerned about the random person tripping on my sidewalk and suing me. 

I joined a couple mastermind groups to  learn and see exactly what it is I'm doing wrong, if anything, get ideas, ask questions, and to ramp up my business to generate more deals and income for next year.

My initial angle once I do enter the investment world would be probably along the lines of what @Scott Nipp was referring to with generating seed capital before pursuing other endeavors. 

The son's attorney should be able to provided the best guidance, rather than some random guy, like me, behind a key board.Okay, well the random guy that posted above me, at the same time, may have better ideas than the attorney.

It does not surprise me that the younger generation is going through a major re-thinking of the owning/renting equation.3.

It's true that you can't depreciation to generate a loss in a given tax year.

Only issue is that if I transition out I need to have a W2 job that will still generate a steady income while I begin the path to real estate investment.