Whatever the soil condition, whether compacted or made impervious by waterproofing compounds, a properly designed piece of engineering work would have all these taken into consideration and a once in 50-year event will only happen once in 50 years and not 3 to 4 times a year.
No amount of engineering could prevent a flood says the sly old man...it should have been no amount of scholar has the in-depth knowledge and understanding of correlated behaviours on the oceans, the seas, channels, straits, rivers, canals, tides, soil conditions, soil compositions, water tables, water pressure, underwater current, weather conditions...and much more... only God knows.
Mechanical and electrical engineering are easier to manage and design with precisions because there are constants you can work with whereas the former has a lot of unpredictable variations. Civil engineerings are sometimes caught off guard by earthquake and tsunami.
Soil alone is not the main cause to flood...it is a combination of those unpredictable variations mentioned earlier that is puzzling.
There is also a possibility Singapore sea level has reached an equilibrium and I strongly believe we have, due to the massive land reclamation.
The 3 to 4 times flood in a year you mentioned could have coincided with the heavy rain and laying of the tunnel across the river mouth coupled with other inherent attributed to over compacted ground, too much buildings, drainage problems, water displacement, marina barrage and God knows what.
My hunch is marina barrage and the underground tunnel across the river mouth is the last straw.
Just hope that fucking old man is weak enough to live longer and witness some of his failures and be fed the same medicine he shafted.