I also started with 4 and loved it. It has the best balance of goofy characters and fun gameplay. 5 is definitely way more fun from a gameplay perspective, but the writing isn't nearly as good. Its just not as endearing as the others. It has its moments, just its inherently not nearly as fun of a story. But I wouldn't recommend any of Disgaea for the story/writing alone. Its good as set dressing, just now what I'm here for.
People swear by Disgaea 1, but I found it such a slog to play. Those early games make it really hard to field a variety of units without it becoming more of a grind. Things like the cheat shop, squads/symbols, made 4/5 way easier and more fun to play. Anyway, 2 was the game where it actually clicked for me(I think its better paced) and 4 was the first one I actually finished. So yea I lean toward getting 5. Most of the fun in those games is messing with systems and that game has the most of them.
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