I think it's more like having a first kid. We know we've got 3-6 months before it starts breathing and there's a tendency to over-prepare because We Want Every

I think it's more like having a first kid. We know we've got 3-6 months before it starts breathing and there's a tendency to over-prepare because We Want Everything To Be Right. We're still not to the point of no-return (haven't quit our jobs yet), but I'm trying to learn everything possible and have everything in place so that when and if that happens we can give it our best shot. #3 is something I'd really thought about, and is probably pretty in sync with what should in fact happen. There unfortunately don't seem to be a lot of smooth migration paths out there, which is what I think tempted me to start looking at some of the more comprehensive systems. There's some overly systematic twitch in me that says, "Get this figured out now, or it's going to bite you in the ass later." But in reality, going with the analogy above, that's probably like planning for a kids teenage years before they're born.