Technically speaking we can play homeless sims. Even if they buy the empty lot, they are still homeless unless we build them a house. But they are not easy to play without a house. I mean, if you want them to get a skill or a certain job position, then you need to be able to play them, increase their skills and what not. If not their own house, then someone else's house. With the upcoming For Rent EP, we might be able to make large apartment buildings with upto 48 sims (and even more if we use cheats), so we could possibly make tiny 1x1 apartments and park all these sims there and pretend that's their PO box not their apartment.