I've always wanted to do this, but the objection raised is "how does this work for people with families?" (partner with a job is one thing, let alone kids).
To Thailand only a few of us went, mostly for the family reasons.
However, to our most recent trip to the Austrian Alps we had almost everyone in the company head over there.
In general we're actually very pro-family. We do have a main office in Barcelona, but everyone is allowed to work from virtually anywhere. Some of us travel and work from remote locations, but for those with families it's also a great benefit to work from home and have more time with their families.
The most capable, adaptable, and accomplished adults I know moved around a bunch as kids. It forces you to learn how to live in the world and get out of your comfort zone. The most anxious, bitter, and underperforming adults I know grew up in the prototypical suburban bubble environment. End meaningless personal anecdote.
I still agree, and in fact kids are often more adaptable than adults. Usually they can handle change, and it is good for the mind to experience different worlds.
Depends on the country / school system. Not all kids have 3 months of "summer break."
I haven't lived in one place longer than two years since I was eight or so. It wasn't the easiest thing in the world, but I wouldn't be the person I am today if I hadn't grown up that way.
I guess there's a happy medium. I've heard horror stories from both ends of the stability spectrum.