She does own a home, and they come back to it in the summer months. They don't worry about taking out the trash since there isn't any while they aren't there. Nothing needs to be done at the house either while your not there. They pay a neighborhood kid $20 a week to cut the grass. There are no bills to pay on the house either since no utilities are being used. The house is paid for too.
You can have any kind of career you want. That's not something that's going to slow us down at all, but we're not like everyone else. My wife is a high school English teacher who will be teaching via the internet when we leave next summer. I recently accepted a work from home job as Senior Buyer for an outdoor gear company. With a telecommuting position your schedule is laid out far in advance for planning purposes. So if you plan accordingly there is zero reason for you to not be available. This position may not work for me since we'll be hiking trails for 30+ days at a time, and 1 trail that will take about 6 months. But that's OK since we've been saving for this over the last couple years.
It worked for us in the past, and it'll work again next summer. If it's something you want you can figure it out. It just depends on how bad you want it. For us, we wanted it bad. We sold our house, and now we have zero debt to our name. We also don't have children, and I know that can play a major roll in such a drastic life change. I'm sure a life on the road with a family is completely different, and I can't give any advise on that aspect. If you need a home, hot water, AC, restaurants, and so on this may not be for you. We've used to living with minimal supplies at our disposal so this works for us.
For us it was simple. We hiking the Appalachian Trail last year, and that opened our eyes to what's around us. It'll be exactly 2 years since the AT when we leave again, and we'll start over.