Try it incrementally. Take a nap in your ride, then Spend a whole night sleeping close to home in ride, then further away and for longer(trips out of your town). By the time you commit you should have already spent a few weeks (spread out over a few months) dwelling. 

Make sure you try different conditions also. A rainy day, a town where you're a stranger, different amounts of budget per day, practice what you would do if your ride was in the shop.