And a local mentor, who has achieve the success I am aiming for and can help me out when I fall on my face or deviate from the tracks.

Real estate seemed like the way to achieve this goal. 7 houses later and it was the best thing that ever happened to me.

On the issue of passive losses, I'd find a good tax advisor.They can help you optimize your tax situation.Activities that are count towards the 750 hour mark are going to involving the property.Acquisition, development, building, management, leasing, etc.

This is achievable when the project cost is no more than 75% of ARV.

And, since my goal is cash flow, that is something I can achieve via a real estate investment group (more than with stocks).  

I'm just not sure what the best solution would be to achieve that automation, short of only selecting tenants with banking accounts and internet access.

I'm happy to make suboptimal financial decisions if it means I sleep better at night -- and in this case, using cash to pay down my house mortgage and paying for things like cars in cash, while borrowing for my real estate investments, achieves that for me.-  I personally don't care much about traveling, but I recognize the value of travel to kids. 

A+ rentals - Homes that achieve a solid 10-15% cash on cash return that need little to no work to rent out.BRRRR - Properties that need a rehab to rent. 

Some of the greatest achievers I have read about in books and watched documentaries on failed and fell flat on their face many times.

My mom worked two jobs just to keep us afloat and barely spent anytime with me, she was doing everything she could.Having a 3 year old, I have a tough time knowing that if I continue in the active income realm (being an employee) I'll never be able to pick up my son from school and help him with his homework and this is something that I may achieve through REI.Once again congrats on your recent success, this is the first domino in your upcoming success!