You can actually play in tandem if you all sign on to the same account.
Create an account lets say make the user name tandem (just so this user does not have Admin authority)
Two or more people (or devices) log on to that account.
One location starts a media file.
The subsequent locations start the same media file.
Plex will give you 2 options
1 Start at the beginning
2 Resume
On the subsequent locations hit resume.
The subsequent locations will start where the first location is at.
Users can keep joining the party and if they all hit resume, you will all pretty much be in sync within reason.
There is latency issues but not too bad.
Works for me around my house in different rooms and across different physical geo-locations.
Latency over remote connections is a little worse depending on any transcoding requirements or network latency but it is workable and mostly achieves what coding tandem users would do.
Just a thought.
Maybe give that a try and let us know how that works for you.
John