My guess is someone who has 100 units is going to get prioritized over someone who has 1 unit. 

For maintenance team management, FieldAware allows technicians schedules to be prioritized and easily tracked with job "Start", "Pause", and "Completed" status reporting, and mobile GPS tracking.Currently, I use MRI X which seems to be specialized for apartment and community manage and allows for a lot of back-end modifications.

I would start by prioritizing the assets and the team.

When I feel as though I have everything covered, my plan was to prioritize and get to work.

I am prioritizing DIRT first and foremost - as you've said, so many of the listings in the low $1million range are rural, limiting near-term appreciation upside significantly.  

Again, I’m prioritizing cash flow over appreciation here. 

I think its great that you're prioritizing them and spending time with them.

That will help you prioritize those three markets or perhaps rule them out and look at others. 

Residents can have a hard time prioritizing where the money should go.

Prioritizing this ahead of time is the only way to make it happen and if you look hard enough you will find a way.