Property Management vs PM Apps

[Pedro Chavarria]

My wife and I recently purchase 2 rental properties in Florida and have been managing them ourselves, however, as we are thinking of moving to NYC we are looking to see how to either automate the process via property management platforms or getting an actual Property Manager. As we are getting more familiar with rentals we want to start purchasing more in the near future and want to move them more as passive investments since we both have "9-5" jobs for now.

2 questions:

1-Any recommendations on the different PM platforms and what would be the best for someone just starting? (looking at Caretaker & RentRedi from the BP site at the moment but not sure what else is out there)

2-Would it make more sense to look for a property manager now even though we only have a few units?

Thanks!