We've been doing this for three years now. This couple seemed to focus on having a year abroad, we've made it our lifestyle, and we're doing a startup (rather than consulting).
I started this as a response to the "how to keep productive" question, but I'll try to address the other questions people have been asking in the thread later on.
We also have the issue of taking some period of time to get back into the productive zone. What we do is spend the visa limit time in each country. For americans in the UK that is 6 months, for instance. So we rented an apartment for 6 months. In the Shengen zone (most of europe) it is 3 months, and last year we spent 2.5 months in berlin.
In both cases we spent most of the time working a normal lifestyle %90 of the time. After our 2.5 months in berlin we spent a couple weeks traveling as tourists (that's where the other 0.5 months went.)
I figure 2 weeks on either side of a relocation are not going to be productive, so might as well spend half of that time, or so, doing tourist stuff. By having such great breaks regularly, we are recharged and I think more productive when we are working.
The weird thing is, indoors, the only thing foreign really is the outlets... so it feels like we're still in the USA, but then you step outdoors and the language, accents and architecture are completely different. So you can "travel" across the globe every day. It is really hard to explain that feeling but it is pretty powerful.
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Taxes & Visas-- As far as governments are concerned we're tourists. We present ourselves this way and we get tourist visas. However, for most visas "tourist" and "business" visas are essentially the same. We don't work in any country in the sense that we don't have a job, we don't participate in their employment schemes. We're taxed like americans (the US taxes your income no matter where it is earned).
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As I mentioned we're doing a startup. (We did one and we're just in the process of pivoting so what the new one is at this point is a little vague.) I don't feel out of the technology scene at all-- I have all the same connections I did before we left, except that I can't go to local unconferneces, but I didn't really get much out of them.
There is one conference that I miss that is done in the USA only, but we started buying the videos for it. Spending hundreds of dollars on conference videos sounds expensive, but it is cheap compared to actually going there (Even from within the USA). I don't really miss the networking opportunities-- and we're now networking with a real international network. EG: we network with the locals wherever we are.
The technology scene really is global.
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Budget:
This is a big one. This inhibits a lot of people. However, if you've got an income from your work, and savings to get by in the USA, you can get buy longer when you're traveling. Even traveling in expensive first world places like europe, right now, we're able to live on the budget we were living on in the USA. Overall, we're actually spending a bit less, and we spend a lot less when we are living in lower cost places (even places in eastern europe, which are "expensive" compared to southeast asia, are cheep.)
So, we could have remained in the USA, and spent the same amount of money. I don't think we would have gotten any more work done, and we would have had a lot less fun. Plus, as our product is global, better understanding of other countries helps.
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Health insurance: We have the health insurance we had in the USA. It covers us globally. There are specific health insurance plans that cover long term travelers and we might switch, we just haven't done so yet.
Neither of us are under 30, nor are we over 50.
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Crazy? You hear a lot of people who knock this idea. Lots of people say "I'd love to do that but I've got responsibilities" or the equivalent.
That's fine... just don't presume we're not doing serious work, we aren't doing a "real" startup or anything lie that. These days startups often have employees spread around the globe... we don't have to carry the whole company with us.
I think people thinks this is harder than it is. Or maybe for some people the idea of living out of a backpack is tough.
Personally, I relish the challenge!
Between my laptop, camera, and assorted stuff, I've got about 7 pounds of clothes etc, and 10 pounds of electronics gear. Every time we-repack, we actually shed some unnecessary stuff. It is a process... but I love it.