I have heard of landlords having success marketing to traveling nurses and to State Department staff returning from posts abroad (I believe they receive a generous stipend for housing as they transition back to the U.S.).

While still allowing you to reap all of the benefits of real estate ownership including not just a return, but also capital appreciation, depreciation, and amortization of the loan (if you have one).This kind of transition is exactly what 1031 exchanges are designed for.

I hope to start him similar to your plan but quickly transition him to sophisticated value adds. 

Hey Alex, From what I am seeing and hearing from the agents/investors that I work with, a lot of investors who own properties are starting to transition from LTR to MTR/STR model, and housing professionals/nurses + the occasional booking on Airbnb/VRBO.  

Offering a gradual increase or some incentives can help ease the transition.

The larger strategy for the big income change has sort of been set to the side while I've been in transition.

I think you would position your future self a lot better if you transitioned a good amount of that equity into some cash flowing assets so you can set yourself up for an early retirement. 

STR and MTR investing is a different animal all together taking you from housing to hospitality and requires more of a time suck than many initially realize. i personally only do long term rentals and students. i do have a property in mind and making the connections to transition it into a sober living home. excited to see how that shakes out. 

Should I hire a local PM company for the short term to make the transition and then after 6-9 months move the PM software?

Successfully transitioning to a new construction company that took over a project already underway was a challenge I managed to overcome.