i think you may consider keeping the day job to ensure a steady flow of income, as the outlook for the coming 2-3 years is rather uncertain.

note that if a down-turn is coming, your worth might be reduced to where you have started if your asset is not mostly cash.

meantime, think about what you want to do with a full-time investment-based career. do you want to work for a financial institution? or you want to start your own firm and start managing portfolio for others? i feel that either way, you may need to get some 'certification' in terms of a master deg, or whatever CFA. granted, you may already have some knowledge, but sometimes they might need to see some papers.

property price is sg is unlikely to drop, it would just stop going up. it takes something really 'hard' to knock down the price of property, and by the time it happens, you may not want to buy. but using rental income to pay for mortgage is a brilliant idea. you may want to talk to an expert in the property market to get some info. i hope you have some friends in the field.

J