old man here.
started skating in 1993 when i was in secondary school. Went for swimming classes at a swimming pool at Surin avenue, now called kovan. not sure if that pool is still around. There were quarter pipes at the basketball court.
Starting skating there. progressed to punngol park, where i landed my first 50-50. met some friends and they brought me to a park opposite monfort secondary school where there are ledges.
when i turn 19, i was good enough to skate at raffles place and memo. never liked dhoby gaut or reebok/starbucks as there are many posers.
mad circle is also a good place if you are keen.
however many of these places which ive mentioned now have skatestoppers. the youth today do not have a chance of street skating unfortunately, your next best thing is sommerset skate park