The complications are what you leave behind. House? Rent? That's a chore especially if you don't have some experience. Cars are easy, park them. Health insurance, we bought a large deductible policy to take off for a year(we were younger too, it was CHEAP back then, now it most certainly is not cheap, but in the big picture, if you're going to go, it's not the reason you won't go). Power of attorney, a good idea, doesn't take too much. Passport is about all you need anywhere in the world, take good care of it.

Money has to be somewhere that is readily available. We used a local bank and got what we needed when we needed it. How much will it take? All of it. Now cash is not so important in most places, that's easier. It's a pain to hide on a boat.

Boat insurance, I think we had it but you can still go without it. A good family member or two. A lot of this stuff has gotten easier with the internet now that I think about it.

Work for us was easy, we lined it up for the following year(one self employed, one on sabbatical).

That stuff above was all pretty easy for us. It was simply an endless list(especially keeping a house and getting it rented, that's work, a house is work) that you finally realized, there was no way you could actually do it all.

The hard part was actually doing the "going". That's not easy, even for a year. You actually have to -- go. That sounds easy but takes some doing.