Wish I'd known that it was difficult to become homeless back when I was. It seemed really easy at the time, all you had to do was get evicted. Not sure how it could be easier now.
I think what they meant was that it's easier than ever to be homeless.
In many places you can't be thrown in jail for being homeless anymore. Many cities have more housing and shelters and free kitchens than ever before. Some places even give you a smartphone and basic plan. Etc.