Talked to my brother about this idea of selling his condo now and buying a cheaper one. He likes the idea. Anyway he says his condo is too big and a 2 bedroom condo is just fine for him, his wife and son. He will also sell his car and stop the maid's services. He is now able to reduce his household expenditures. So, his wife's income plus his potential dividend income in total will be more than his total household expenses. This gives him less worries and he will be able to focus on his job search. If he can't get a new job, he plans to set up his own business as a consultant. This business doesn't require much overhead as he can work from home. If he needs to meet his clients, he can just take the MRT and bus.