Advice: automated playout and scheduling, and live/automated transitions

The Volunteer who has handled automation/overnight for CJNU has decided to leave our station after a number of years, and we’re scrambling somewhat to adequately cover the tasks he was performing for the station.
He looked after all of the programming and scheduling for everything that runs in automation, and the transitions from automation to live (and vice versa). This has been done through SAM broadcaster as a playout system, and a piece of software called Music 1 which used a GUI to enable the programming music, spots, etc., and generates scripts that are used by SAM.
I’m wondering if you might have some advice/expertise on how you handle these things at your stations, what software or solutions you use, and how long on average it might take to program an average day at your station.
Thanks so much!
CFRC rebroadcasts its daily content overnight from 12 am to 7 am (save sunday nights when we have a pre-recorded programming airing until 2 am).  All of our nighttime volunteers are trained on use of Megaseg, the automation software we use.  The process is that our nighttime volunteers download rebroadcasts from the current day from our archive, load them into onto the desktop and into the Megaseg system.  Staff also use VNC viewer to monitor and control Megaseg remotely when necessary.  Generally, this system runs well for us, though it's a matter of communicating VERY well and VERY clearly to all of our evening volunteers what they need to do and when-for example, sometimes a live programmer can't make it in and pre-records their own show...that means the individual whose program precedes theirs is responsible for loading the overnight rebroadcasts into megaseg (or staff via our VNC viewer).

Hope that helps!

If you've already paid for SAM and Music1, then it is
probably in your best interest (at least for now) for
someone at the station to take some time to learn how these
2 pieces of software work.  SAM is for playout, and Music 1
does the scheduling.

Chances are you already have clocks and schedule templates
built in Music 1, I'm sure the playlist exports for
exporting from Music 1 to SAM are already created, so you
should be able to crank out the schedules as needed
relatively easily.  There are youtube videos and other
how-to that can cover the basics for both Music 1 and SAM -
Google is your friend.

If everything is built in these 2 pieces of software, and
with the hecticness of when someone leaves, this is probably
not the best time to switch to a different system. (just my
$0.02)

Insight and wisdom much appreciated.
The two pieces of software generally work reasonably well - it’s just a steep learning curve at first.

I’m not panicking about this transition - but there’s a certain lack of knowledge being passed along, and this individual is leaving in shorter than ideal notice... so the few of us that are trying to keep the ball rolling are really starting at the ground floor.
Mid to long term, a software change could be in the cards. Short to mid, we just want to stay on the air, and meet promises we’ve made to sponsors/advertisers, as well as keep pre-recorded shows on the air.
It’s always good to learn from how everyone else handles these challenges!

Yes, given the situation that you've described, the best for
now is to stick with what you currently have.

No matter what you use you'll have a learning curve.
Sticking with your current system - at least you know that
it has worked in the past for you.  No point trying to bite
off more then necessary at this point.

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