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.

Yes, they are more difficult to sell (the average homeowner won't be able to buy them, but other investors ARE constantly looking for apartment building offerings- especially the smaller, easier to manage ones, perhaps you reduce the rent for a handy tenant to be the 'maintenance guy', and a smaller complex he can handle in addition to his 'day job'... with multiple units, you get more rent money 'per door'- and if one or two is in transition (not rented), you have the others to make up the shortfall. 

We have transitioned one of our properties just recently to us owning them and using cards.

That is when they usually start to transition in to asset based options such as DSCR 

That will get you an additional 45 days (a lifetime in a transitional market in an election year) to identify that elusive replacement property.