Sorry to say but these people really don’t deserve pity. Provide you with shelter you say you will lose your freedom, you rather pitch tent in public area. FREEDOM COMES WITH A PRICE. Live within your means and you will not end up like this. Keep complaining about rich people holding on to their HDB while owning private property. You know what? People can afford to own multiple properties because they worked hard for it. You think money drop from the sky? Stop complaining and blaming PAP for everything. Blame yourself for not making proper housing decision and end up homeless. Blame yourself for not seeking help from the correct channels. Blame yourself for your incapacity. What era already still want the government to spoon feed you.
"I keep on applying to jobs, aiming for bigger companies but there isn't a lot I qualify for although I think I have a decent portfolio and amount of experience."