The context of Matthew 8:20 is Jesus communicating to a teacher of religious law the cost of comfort to follow him relative to to his typical lifestyle, because Jesus was an itinerate minster. By using hyperbole, Jesus isn't literally saying he's destitute homeless. He clearly had a home base and a network of places to stay while ministering away from home. He's saying, "This isn't going to be easy compared to how you're used to living. It's going to cost you your comfort and some material luxuries to follow me during this period of my ministry." In addition, Jesus sometimes used offensive, non literally language to test whether people were willing to follow the Truth, he himself, to see if they were capable to looking past uncomfortable language to what was valuable and worth it behind it.