I think it’s a risk thing: in the last 300 years, there have been four episodes where the Ironborn have been actively attacking Westerosi ships/mainland:
- Dalton Greyjoy’s reaving during and after the Dance: ~3 years.
- Dagon Greyjoy’s reaving after the Great Spring Sickness: at least 3 years.
- Balon Greyjoy’s rebellion: 1 year.
- Ironborn invasions during War of Five Kings: 3 years so far.
So that’s 10 years (although could be more, because we don’t know when Dagon was brought down) out of 300, or 3.3% of the time.
The question is: is a 3.3% risk of piracy worth it?