One of the biggest obstacles for people to overcome when taking off on a long-term, round the world trip is the housing situation, particularly for those who own. Some may feel completely tied down, especially those who are underwater on their mortgages. But just because you own a home doesn’t mean you are stuck. It doesn’t mean you can’t take a long-term trip. It just means you’re going to have to work a bit harder and be a bit more creative in your planning.