LiveWorkAnywhere has a network/community of traveling entrepreneurs and 
freelancers; their founder is Libby Tucker and she'd be a great person to 
talk to. She's a friend of mine with years of experience doing just what 
you're talking about and will have a lot of insight to share. 

Personally I think it's a great idea, though when traveling I stick to 
working out of coworking spaces when in cities, and skip working while 
visiting more far-flung places.

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