There are many reasons to get old flats - of course for the familiar feeling and surroundings that we are so used to - we have to pay a premium.
The other reason is of course for SERS but in this aspect, the location is important. It has to be close to MRT stations or potential-MRT stations.
On the other hand, people are also so hung-up on the place.. like die-die must stay in the East or particular location. It is not wrong to have this type of wants... but like what powder said - you have to pay a premium for something you like. But ask yourself, why you like the place? Other than for nostalgic reasons, there should be other equally attractive place to live in.
I have lived in the central (chinatown & queenstown), west (clementi, west coast), north-west, north, north-east and I am more like a nomad.
Old estates are good and convenient but some of them the traffic are bad and they can be very noisy.
Actually, the new estates are fine as well - only thing is of course you won't get all the nice food that is available in the older estate. But with a car, there is not much of a problem.
Some of the newer estates (like punggol) is so quiet.
For me, in terms of living.. I would like people to think and step-out of their comfort zone. What you are familiar with and comfortable with may not be always the best.