“You can still see it in Eretz Yisrael today.
True, although easier when everyone else around you also has nothing.”
True, but still not simple. And there are always those who have less than others. And often, people take turns being the one who has less than others, so many people get to be in that situation.
But, if you are going to be poor, it is definitely MUCH more geshmak to be poor in Eretz Yisrael where there is so much more ruchnius, so you don’t need the gashmius as much!!! And where there is so much more hashagacha pratis (see the Ramban – sorry I don’t have the source,and I’m too busy making potato kugel to look it up :))