I did this for over a year with my wife and kid. I originally planned on quitting my job as a government contract and doing only freelance, but instead ended up working things out so I could work remotely ~4-6 hours a day. It was nice having a fixed schedule and fixed paycheck and it left my mind free to enjoy Uruguay, Brazil and Argentina.

I can't recommend it highly enough, it was surprisingly easy to do and definitely one of the best years of my life.