The Text cues are routed to a stage which goes to an (unused) NDI output. The Playlist group is set to loop, and also set to play next on a second trigger.
When you start the Playlist group, the first song plays, completes, and follows to the Text cue which plays invisibly to the unused NDI output.
When you start the Playlist again, it advances to the second song. When that song concludes, it follows to the second Text cue.
Repeat as much as you need.
There is, however, a dramatically simpler solution. Create a second cue list and set it up like this:
Give the cue list a hotkey or MIDI trigger, or put a bunch of Start cues which target this list in the main cue list.
Every time the cue list is triggered, it will either play the first song, or play the second song and then return the playhead to the first song. This solution can also, clearly, work with any number of songs, not just two.