My honest opinion is for you to upgrade to a condo if your existing hdb has been paid for and u have extra cash for a condo. If your flat has been paid for, then buy another condo, rent out the flat and use the cash for the installment. Purchasing condo is a form of forced savings and these money will come in handy when u r nearing retirement age, otherwise you will have to work till 91.

Finance sectors depending on which companies you are in, does your company have restructuring often and the tendencies to get rid of 'expensive' people, if yes, you may be in for some trouble. Some banks though, do not practice retrenchment and if your company is a 'safe' one, you dont have to worry. In the event that you are retrenched, remember to lower you expectations when you are looking out. There's no guarrantee that a job is yours forever, but i will not worry too much. Risk wise I can't advise, but my experience as a recruiter tells me managerial roles at 200k pa gets retrenched as well. But like i have said, if you company is a responsible and profitable one, you don't have to worry.