From my experience and observation:
a. Subodrinate Courts CarPark - There is a URA booth there. So
coupon is a must.
b. MOM Building Carpark - The URA personnel are permanently based
there.
c. Geylang (all the lorongs) - The URA personnel has no place to
hide so don't take any chance. They are always around.
d. HDB Carparks - They usually comes on the 1st week of the month;
to check if you got renew your season parkiing ticket. Their main
data terminal will show who did not renew and which carpark (my
assumption). Timing: 8 am to 9 am and 8 pm to 9.30 pm. So the most
safest period to park at HDB is the hours in between.
Oh yes, night time - the male attendants on scooter will come,
usually on weekend nights, especially Saturday( after
midnight).
Cheers!