Probably just to act as a relatable hopeless situation to the Dominion war
Apparently it was an Ira Behr thing:
Ira Steven Behr has a fascination with the Battle of the Alamo and he and Hans Beimler included a reference in "Wrongs Darker Than Death or Night". Later, Ronald D. Moore and Rene Echevarria began to include references in their scripts. Some fans thought that the writers were hinting the series would end with a battle like the Alamo, which the writers had no intention of doing, having already featured such scenes in "The Way of the Warrior". (Star Trek: Deep Space Nine Companion, p. ?)
I just saw it as two friends getting obsessed over an impossible task... As ya do
They'd previously fought and won many other simulations of other wars together and decided to make it harder. Didn't feel super out of place tbh, especially with the two involved.
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