After 45 + years as a real estate investor, broker, lender, fund manager and syndicator, I’ve become aware that the “dream” of many investors and investor “hopefuls” is to be able to generate enough cash flow to live off their real estate holdings and accumulate enough wealth to make “work” optional.

A few that sell and manage, or know management companies.  

If you have no facts, then yes an appraisal can be your ticket, but also keep in mind how your state manages assessed values.

My landlords use Azibo for management and RentSpree for screening, but there are a million options.

How much of a pain will it be to manage tenants?

I'm born and raised in Houston and now work with a full service long-term rental management managing over 300 doors - all SF or MU (up to 4 unit).

I'm considering partnering with a non-profit that would manage the sober-living program; with me just providing the house passively for rent on a per bed basis. 

You would need a good property manager, he is also a real estate agent.

On a more enterprise scale, I employ RevMax software as well as a fractional revenue manager who looks at the prices daily on a market level and a comp set level. 

Property Manager – This is another one I really need help from the bigger pockets community in the local area.