Dakota is deceving because it is so close to Geylang, and the condos
there are right next to some older HDBs. But on the other side just over the river, you have one of the richest parts of Singapore (Tanjong Katong) loaded with landed houses larger than castles. You are a short 10 minute walk to Tanjong Katong Rd, which has a good amount of nice bars, cafes, and places to eat. You have a park connector along the river (exercise/walking/biking trail). You're right next to the MRT. 2 minute walk.
The most important question is what Curious George asked: What is your expected commute time? If you don't need to be within a 2 minute walk of the MRT station I would look on the other side of Tanjong Katong Rd. Something between Haig Rd on the west, Still Rd on the east, Crane Rd/Joo Chiat Place on the north, and the beach on the south. This will give you an amazing amount of options for shopping, food, and local entertainment. You're a bit farther from the MRT, but depending on where you're commuting to there are dozens of bus lines, express busses, and private buses. I live right in the center of that square and can walk to Dakota MRT in 15 minutes. (Or, take a 5 minute/$6 cab ride to/from it)