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Pineapple said:

That was the start of it, but it seems to have become a bit deeper as it went on. The first ones were more of a nod to the past, and more of a fan-service-y approach. There are 5 different gametypes/maps, and each had 3 different groups of enemies on it (so 3 DLCs with the same map, for each of the 5 maps).  Those 15 DLC (5x3) were the first series.

The second series seems to be more original. The first DLC is a simple map and adds 92 (apparently - source is serenesforest) new support conversations between your characters. The second in the second series is a map that has your units reduced to 1hp every time your turn starts. 
The third one in the second series is also more unique, where you defend 5 different NPCs, in different parts of the map.
Then the fourth one (and last to release so far) you seem to have to chase 4 enemies trying to escape from you.

So the first series seems decently interesting, while the second ones seems like it could be a lot of fun.

Edit: Overall, it's more of Intelligent Systems starting out with what they know is going to be accepted, and then trying new stuff.

Huh. I stopped following as religiously after the first ten or so, since it seemed like they'd all be cut from the same cloth. Apparently that was sloppy of me.