In many ways those who want this probably would do better in a job than in an entrepreneurial role.And that's with regards to good coaching programs.

The country simply does not have enough affordable housing units, and the new supply of affordable housing units is not keeping up with new demand.

There is not the depth of what you're asking.

When I was in college, my landlord would just walk into the house uninvited without even knocking.

I also had horrific PMs, particularly involved with a 48 unit apartment complex in Houston.  

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

Find the style that people are doing in the area then find equivalent options for materials at local supply houses.

I don't know if that is included in the total rent numbers the owner supplied. 

I work in GA.  

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.