A friend told me he is seriously considering selling his fully paid 5 room HDB flat in RCR to buy 2 shoebox apartments so that he could stay in one and rent out the other for cash flow. Hopefully, property prices would go up and he could benefit from capital gain by selling one. I told him that he would be moving from being debt free to being indebted. There is no guarantee that the monthly rental could cover the mortgage payments (plus the much higher monthly maintenance and property tax of a condo). He says he just wants to make money but how sure is he that he would make money this way? I see a strong speculative flavour in his hope that property prices would go up. I told him if he thinks property prices would double in 10 years like it did in the recent past, that is speculation......