This isn't going to be easy or quick !
I suggest you start by building a PlayIt Live system and learning how to use it.
If you could defer the change of playout system until your format change that would simplify matters but it may b too much change in one go.
In particular, folders based on your rotation choices make the process much easier. Although you can do it "your way", you will find the "monitored folders" feature works well if a folder corresponds to a music category.
You may find the rotation rules and scheduling a bit limited, particularly for commercials (without the paid "Advance Scheduling Module" upgrade).
The scheduling of PlayIt Live is based on clocks and the hard time markers are the way to make things run to time.
There are various ways of dealing with "complete shows" but probably the best way of automatically playing a file is to have the latest version of the show as the only file in a folder (by some means) and let the scheduler put it in the schedule. Other methods are a bit "manual".
I use PlayIt Live with 256kb/s MP3 files and they generally sound OK but had I started ripping my music now I might have chosen a different format.
Unless you have a fairly limited library, re-ripping CDs is going to be quite a job.
Unless there is some reason not to do so my rough suggested workflow would be:
This was written with little sleep while on a phone so I hope it all made sense, at least the original post was. I want to get off of OTS AV/DJ as soon as possible and get away from that nightmare. I mean its not real broadcasting software by any means, at least nothing that resembles anything in the broadcast realm I've ever seen.
On to music, my big concern is that the format change. I don't know when that will happen but it will. Right now they have categories for their music, so a song might be in one area but might also be found in hits (they are using hits for things they want to hear more often than others). I want to be able to tag different songs to different categories rather than move them to folders and do all of that monitoring. I've done categorization even on Scott Studio back in the day so I know thats something that should be able to be done here.
We have to get a way to have this system play an evergreen item during times when I have long form programs playing. For example, if a 30 minute show goes missing I want it to pull from a selected show or folder to use instead and hopefully without user intervention. I'm unmanned a majority of the time so this is a concern.
Talk to me about the advanced scheduling upgrade; what features will it offer me that I don't have now besides advertisement campaigns? I'm non profit and I can't run commercials. What I'm doing is playing some PSAs and such from folders where this won't necessarily matter if it airs or not. But if there are features that will allow better opportunities I'm for that.
What are you doing for audio file formats instead of MP3? The original files aren't going to be available and in OTS DJ they imported them in 160kbps. I don't have an option on that but to just go with the files that aren't done correctly. We are moving to 320kbps (480kbps is used for over the air television broadcast by the way) but I still don't like being in MP3. I also have Barix boxes in my audio chain which have their own MP3 compression so I'm not getting totally what I want yet.
I've not tried the "Advance Scheduling Upgrade" so can't comment on that but there is a video on scheduling which, with the manual should explain how this works in PlayIt Live
If you made a clock with your "evergreen" items and scheduled it in the hour then it would fill a time slot with a selection from that category.
Track Groups and Playout Patterns may approach what you want to do with music categorisation but, once again, I think you need to experiment with what is possible.
Personally I use MP3s, the system will play WAVs, MP3s, WMAs or MP4s.
The most likely problem with files other than MP3s will be the metadata.
As to bit rates, all things being equal, the best approach is to use uncompressed audio early in the chain and then only use compression at emission/distribution.
The Barix units are not, intrinsically a problem but add a further bit rate reduction stage. depending on what you are doing it may be possible to run them at a higher bitrate.
The 160kb/s OTS files are unfortunate but "you are where you are", you can either use them or replace them. Either will be lots of work.