I have a few comments...
Regarding any flooding, it's important to be specific. To say the northside has a tendency to flood is misleading.
Certain areas of the northside have a tendency to flood, most of it doesn't. You have to be specific about what streets in particular you are talking about. Some are more prone than others, and that can vary even on a single street. There are houses on the river that don't flood unless a monumental rain comes through, like a 100-year (or 500-year?) storm like Hurricane Floyd, where over 13 inches fell in a matter of a couple of days and an upstream dam broke. Even then, some houses on the river only got minor flooding, if that. On the other hand, there are small areas not on the river that tend to flood more often.
You have to take each house individually and do your homework. Houses on the south side can flood as well, given enough rain, as Cranford is a town where "the river runs through it." But management of the river has gotten better, and its level is routinely lowered when very heavy rains are forecast. The river is part of Cranford, and it is that same river that helps provide Cranford with charm, beauty, and activities that other towns can't offer. Incidentally, quite a number of river properties are among the most sought-after and expensive homes in the town.
As far as northside/southside issues are concerned, yes, there is a difference depending on what aspects you are discussing.
From a day-to-day living standpoint, there is little difference in the quality of life so far as I can see. From a housing perspective, it is true that in general, the largest, most expensive homes on the largest lots are found on the northside. The southside has a much greater diversity of smaller homes on any given street. It is common to find a mix of bungalows, split levels, colonials, and even victorians on a single street, depending on what part of the southside you are looking. It is more apparent because the lots are smaller and houses closer together.
Home values on the northside are, in almost all cases, higher. Whether you get more house for your money on the south side is debatable, as you have to consider the house itself and the street it is on.
The southside of Cranford borders Roselle, Linden, Clark, Westfield, and Garwood. While Linden as a whole may be the least desirable, it is by no means an Elizabeth or Hillside, and it isn't as if there's a slum as soon as you cross the dividing line. If you like Polish food, Linden is the place to go, and one of the best burgers you'll ever have can be found there. Here's a map of the border towns:
The southside does have the freight line, but unless you live right next to it, you may seldon notice it. There are only two streets in Cranford where the train crosses the road, and both are elevated. There are actually very few streets with houses that are in close proximity to the tracks through Cranford.
The southside houses the Cranford indoor pool and faciities, the recently rebuilt Community Center and Library, and is home to Sherman, Lincoln, Johnson, and Buchanan parks, and partly borders Unami Park.
The northside has the outdoor pool, Sperry, McConnell, Hampton, Hanson, Adams, Girl Scout (with the clay tennis courts), Memorial, and Nomahagen parks. Most outdoor Cranford concerts and fairs are held in Nomehagen park, along with the fireworks.
The Northside has the Canoe club, and hosts the annual Canoe races and the duck derby. Yes, the High School is located there as well, as is Union County College, home to the Sperry Observatory.
Regarding kids playing outside, I can't really say what differences there might be between the north and south side. It could just be that you noticed this coincidentally on a specific day. I don't think the age demographics are much different throughout Cranford.
For the most part, I consider people in Cranford to be a little more conservative, meaning tending to be somewhat less flashy about their net worth, than say, Westfield. That's a very general comment, though, and you have to take it on a case by case basis. There just seems to be less conspicuous consumption in Cranford. People are generally nice and friendly, north or south side.
If you are considering the south or north side, you may get better information if you can be more specific about what street you are thinking about.
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South Cranford questions
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