He didn't even experience real homelessness. The fear that comes from having no safety net at all, wondering how many times you're going to eat that week, being in chronic pain but having no way to address it, Only sleeping a few hours a night for days on end cause it's too damn cold an you keep getting chased off. Simply knowing that if it ever really get to much you can go back to comfort doesn't let you experience the true terror of knowing your only way out might be in box.