I am a developer too. I tried a 5 month work abroad test last year, staying almost a month in each Iceland, Germany, Spain, Italy and France, and visiting other countries during the trip.
I enjoyed the time zone difference while in Europe for the 5 months last year. In fact, I was able to radically increase my productivity and billings. The time shift worked out great for my dev work, allowing me to really get tons of work done before clients on the east coast came online or were even awake . It was difficult when US west coast clients wanted some off hours work done, but it’s easy to schedule and a tiny adjustment. I loved having my free time being early morning/day with my 3 kids, exploring, traveling, or even just going to the grocery store or public markets, or doing the necessary errands, like banking, then working afternoon to midnight. Most of that time my kids are sleeping anyhow, so I feel like I am missing out less and I can be more involved. I am a night person anyhow so it works out better for me than when I am on the west coast, usually 3 months out of the year. I hate being up and available for my clients 9am ET when it’s 6am PT, and dread the 8am ET meetings/conference calls. I am trying to figure out how I can get my family to Hawaii for a number of months to test things out. I hadn’t been back there for more than 20 years and I’d like to share that experience with them.
Most of my clients are in the US on the east coast, a few on the west coast and middle US, and one in Japan. Most communication is over email, then skype, then phone. Use Vonage, project Fi or similar to bring your phone number where ever you go. My business is all about providing excellent customer service, and I always answer my clients calls, even at 3am, regardless of time zone.
As for taxes - I have not found a good solution. I am hesitant to setup a foreign corporation, that would employ myself and wife. Currently we are both self employed. So that means we are stuck paying the SE Tax. From my understanding, the FEIE would only apply if we were employed by a corporation, not self employed. As it stands now, with deductions, i401k and retirement savings, we are only hit with a 12% overall tax. I’d love to see this reduced, but having found a practical way to do it yet, plus we haven’t been out of the us for the 330 days to qualify in any given tax year.
It would be great to find some other like minded families that wanted to setup a collection of pied-à-terre in various countries to inhabit in a round robin fashion to perpetually travel and explore.