If they have excellent credit, great job history, great references and you met them and got a good feel. 

I am now working with Logical Property Management and they have done a great job thus far. 

Because one of my first questions dealt with the job’s complexity, to which I asked the loan officer to review with underwriting if this would be a problem.

You will find some of the people you market to (friends,family, former job associates,etc.) will say ( I am an agent, I used to be an agent, I already know someone I use who is an agent,etc.)This is one of the toughest professions in the world.

They would do a stellar job helping you navigate and landing hand managing :)

That is the issue I am having now as my wife and I have great paying jobs and just cleared all our debt.

His roadmap for retirement is $500k liquid assets, paid off primary home, and more than 1 income source (real estate, part time job, social security if old enough, etc.).

I have no w2 job, a lot of toys (need to get a plane), can do what I want, can assist my son to find his way in life (he is leading his 2nd rehab) and if I wanted I have generational wealth (I have given away a lot money the last few years).  

It would be best to befriend a local contractor or even help one out on a job to see any differences from your past eight years doing it in another country.

It might be helpful to narrow down your options by focusing and researching for markets with strong rental demand, growing job markets, and property prices that fit within your budget.