We are renting a small 1 bd apt. downsized our outgo by $700 +/-.

As soon as the legal occupant moves out, go take possession of the house.

The property management company isn't going to price gouge by charging me another tenant placement fee which is awesome.The security deposit will cover the turnover fees, and any loss of rent.We're going to work on keeping the out-going tenant happy while we find a new one.Hopefully next one goes a bit smoother!

They can give you notice whenever, you still have 30 or 60 days until they actually move out.  Going

If check-in/check-out goes well, two-thirds of what they remember is automatically positive. 

On the other hand, if you get it re-rented prior to the end of that mandatory period, you cannot double dip...you must pro-rate the outgoing and the incoming based on start of incoming term.

Now if you're a glutton for punishment, don't mind cold calling and/or door knocking, have the gift of gab and/or are exceptionally outgoing, and have a war chest of money to spend on marketing and your own living expenses while not getting paid for months on end...then by all means become a real estate agent. 

I've been using Sherpa, and some of the new regulations have definitely posed a challenge with how the outgoing texts need to read.

Are you outgoing and have a generally good business head?  

The financial terms of the sublease would be negotiated between the outgoing and incoming Tenants.