Buying a house in Singapore, using your CPF is a prudent measure but you must know what is the upper limit. If you over-stretch yourself, ie you buy a house and take a long loan and your CPF at the current moment cannot fully service the loan (and you have to use more than 10-15% of your pay for cash), I'll take it as stretching yourself. Of course it all depends on how much cash you have upfront (the more the better), all things being equal.
It is important we buy a house within our capability otherwise the interest of the big housing loan over the long period will kill you - very slowly that you may not notice.
In land scarce singapore buying a house is a good bet - irregardless of location. Those in choice district are for the rich. For most of us, any location that is convienient for us is good enough.
The way I look at it property price in general will appreciate over time. Except when in the high-end apartments in choice district - this is where the rich will play, appreciation will be slow and steady. There won't be spectacular jumps like in the 90s or big fall like in 1998.
One thing for sure, the capitals control are in for housing loan, ie you cannot have 100% housing loan. In the 80s/90s you can even have 110% housing loan. So, in a way, property price will not shoot up spectacularly as it is much more difficult and expensive to speculate.
Property to get rental income is no longer very attractive - still attractive if you really have the cash. It does not make sense cause the rental yield is very low and it is not sufficient to cover your interest payment. It used to be very attractive (> 10%), I used to have an apartment that I bought for < 300K and I got rental of 3.5K per month and my loan payment is only 1.5K per month. Then when the property boomed in the mid 90s, I sold my apartment for big profit rather than take slow monthly gains.
Take note that every property transaction will make you poorer - the agent's commission, the stamp duty, the legal fees etc etc. Unless you are rich otherwise it is difficult to play properly in the property market.
Actually rental is a viable option as well especially if you are not sure of your long term directions. People always think that your CPF money is wasted if you are not using it - not true. You can use your CPF money to pay interest of your housing loan (the bank taking away your CPF money) or if you keep it there it can be a sizeable savings when you retire. There is really no single best way in dealing with it - it really depends on the individual factors involved.
As for car, if you are thinking of a car as a means of transport (for convienience or necessity) then a second-hand car is really a good deal financially. Yes, you won;t have the smell of a new car but because the second hand car is cheaper (although you may end up paying almost the same monthly installment as a new car) but in reality you got a good deal especially when things are not certain and you won't lose much if you decide to sell your second hand car.
The value of a car drop is the biggest during the first year and you won't have to be a rocket scientist that you can have a bargain for 1 year old car. Or if you really want it cheap, you can have a 8/9 year old car or even COE cars.
Actually it make perfect sense for first time car owner because you won't worry about banging your car because it is a old car. If you bang your brand new car you heart will feel the ache.