I spent the last year traveling with our two kids (5 and 2). As far as the amount of money you can make, it varies widely by area. I've been working in southern CA and making more than $2k a week. The cost of benefits IS expensive - the travel agency insurance policies were insanely expensive and didn't have the kind of coverage I wanted. We got our health insurance on the state exchange instead and it was much more affordable for better coverage. It's probably the only downside of this kind of work, and it's obviously still very manageable making as much money as I have this past year! Best of luck!