Also I'm wondering if anyone would hazard to perhaps offer a prediction or judge how likley this is to succeed (maybe on predictionbook)?

For PB, you need relatively precise predictions. What exactly do you mean by 'succeed'?

There are a number of ways you could operationalize this - for example, you could go by whether the Seasteading foundation is still active in a given year, whether its budget is above or below a certain amount, whether Thiel is still donating (and how much). One could make predictions about permanent habitats and number of people aboard, and hope that there aren't unfortunate corner cases like seasteads which only leave port during summer or oil rigs with unclear ownership. And so on.