The people you see who live on the streets long term usually are either severely mentally ill or have substance abuse problems. Any JWs who have these kinds of issues would have been kicked out of the organization long before they became homeless. I knew of a case where a brother was disfellowshipped because he heard voices. Having met him, I was pretty sure he was schizophrenic, but the elders assumed he was demonized. Problem solved for them, nope they don't have a homeless problem.
For JWs that don't have these issues, they may avoid being homeless, but they are more likely, in my experience, to rely on food stamps, rental assistance and welfare. Having followed the advice to not pursue higher education, they are less likely to have well paying jobs. And since the Watchtower tells people they should rely on Jehovah and put Kingdom interests first, they are less likely to plan for retirement or save money.
I realize there are exceptions to this, some JWs do get an education, have decent jobs and save money, but I think that the Watchtower teachings do tend to discourage responsibility and planning for the future.