Originally Posted by Gypsea
At which time I could try to convince her to dump the house? Of course, she knows nothing about any of this at the moment. Just wondering how most women out there would feel about this scenario?
Let me start with the caveat that you should be asking HER this question, not a bunch of strangers on the internet. If your relationship is such that you can't talk about what's on your minds, you will NOT survive the close quarters of living aboard. That said ...
You dump the house when you both realize that it's just not supporting your goals anymore. You move aboard (or she meets you in Hawaii and joins you aboard) and after a while you realize that you don't miss the house. That's when you let it go. But there's lots of ways to achieve that: you can put your stuff in storage and rent the house until you're sure living aboard suits you both. Expensive? Not compared to peace of mind, the sometimes very real sadness of parting with some sentimental things, and much cheaper than repurchasing everything if it doesn't work out.
One other thought - seasickness is one of the few things that gets better as you age and your sensitivity decreases. Depending on when she last tried sailing, might be worth another go.