I believe you can do what you want without scripting.
My suggestion is in the editor create a Power Daily mechanic for the Skald class. Take a look at how MagPwrDai is set up for mages. Make sure "Overrides" is set to Daily Power Mechanics and "Don't Bootstrap" is checked.
Then edit "Class Powers per Level" is set up correctly for the powers.
Each row represents a level and the columns represent the level of the power.
So it should be something like:
Row 1: 1 1
...
Row 4: 1 1
Row 5: 1 1 5 5
..
Row 8: 1 1 5 5
Row 9: 1 1 5 5 9 9
..
Row 14: 1 1 5 5 9 9
Row 15: 1 1 5 5 9 9 15
..
Row 18: 1 1 5 5 9 9 15
Row 19: 1 1 5 5 9 9 15 19
..
Row 24: 1 1 5 5 9 9 15 19
Row 25: 1 1 5 5 9 9 15 19 25
..
Row 28: 1 1 5 5 9 9 15 19 25
Row 29: 1 1 5 5 9 9 15 19 25 29
..
Then add this new mechanic as a bootstrap of Skald class.
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