Best of luck with the goal. I've got the exact opportunity you describe right now, but with a wife on maternity leave, a 3 year old, and a 1 month old. We both get to work from home when she does work. Once the kids get to 2 years old, you need to buy them a plane ticket. So we are leaving on a road trip around the Western USA Friday.

Sorry for the cheap shot, but I think you should lose the Apple devices if you want ease of travel. Android global GSM FTW.