So just as everyone else has said in this thread -- sounds like you have enough of a cushion to do just about whatever you damn well please for at least 2 years (taking into the account the possibility that you decided to live as a rockstar at ~5x above your current means)
What I do want to say -- and I'm really unsure that I should be saying it at all (since I'm not your dad, but then again, this is the internet)
Maybe you should start at least considering settling down somewhere? I don't mean settle down somewhere and enter a company you hate for the rest of your life just for job security, but more like pick a place (or search for) a place you want to be in for a long time
With IT/software skills like yours, I doubt there are many people who won't see your value at a technical company, and that will enable you to get a job in most places, but being transient forever (even if you're writing awesome software) doesn't seem like a wholesome plan
I'm definitely assuming too much, and I don't know anything (outside of this post) about you or your goals, but just figured I should at least make the point
Also, your Honolulu-as-a-place-to-live idea sounds amazing
What I do want to say -- and I'm really unsure that I should be saying it at all (since I'm not your dad, but then again, this is the internet)
Maybe you should start at least considering settling down somewhere? I don't mean settle down somewhere and enter a company you hate for the rest of your life just for job security, but more like pick a place (or search for) a place you want to be in for a long time
With IT/software skills like yours, I doubt there are many people who won't see your value at a technical company, and that will enable you to get a job in most places, but being transient forever (even if you're writing awesome software) doesn't seem like a wholesome plan
I'm definitely assuming too much, and I don't know anything (outside of this post) about you or your goals, but just figured I should at least make the point
Also, your Honolulu-as-a-place-to-live idea sounds amazing