I feel like I'm a good candidate to jump in, as I'm halfway through my drive to California for my sister's destination wedding. I'd say clear it with your immediate families if you're close with them, if you get the green light, go nuts.
It can be a huge financial strain, and also takes a week or two of people's vacations.
We have a 6 week old baby, so at first I was kind of perturbed, but now I'm actually really glad as it's forced us out of our comfort zone, and if this goes ok, it opens the door to future adventures. My wife and kid are flying out, then we're taking the opportunity to drive up the coast after to return home, something I've always wanted to do. If this goes well, we'll probably do things we wouldn't have considered with the baby or future babies. Which a colicky 6 week old... we may just learn a very painful lesson... haha.
Also, it's forcing us to have a family vacation, something we haven't done all together in years. I think it will be a blast.
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