I’d like to build a team and have a property management company involved that way I can utilize my time and efforts on other things besides maintenance. 

Take into account the travel time, phone / video time, mistakes along with all the other economic factors.

At the time, both units were occupeid with month-to-month tenants who had lived there for 9+ years each.

I like the idea of short/mid term rentals more then the long term...one big reason is not having to move all of his stuff...or at least being able to take my time.

People sign leases stating that they agree to no pet policies all the time, yet, they still bring them in.

(a) From the time of the sale until a redemption, the purchaser is entitled to receive from the person in possession the rents and profits from the property or the value of the use and occupation of the property.

I’ve done Zillow, filtered it based on Bathroom/bedroom size, home type, etc.I’ve found a few but in the event where houses for rent don’t show up (due to time of posting ?)

It's the most susceptible and bottomless aspect of consumer discretionary income.

Something that makes my situation a bit more difficult is that I have a job in Hawaii (6 hour time difference from EST. right now).

Check your local rules, but where I have rentals, the tenants need to be out by 1 pm on the last day of the month and you can organize with the new tenant what time they are moving in (eg 11 am).