The Raids into Ithilien were risky to say the best... I think they were conducted mostly for the moral of Gondor, to hear about victories even though the times were dark... Hope can be the strongest tool for keeping the civilian populous united. After all, with Berigond of the Gaurd on your side...
Gondor couldnt afford to let their enemies walk at will through the Land, otherwise more and more would be drawn to Sauron's cause. With the fear of an ambush and death less southern and eastern savages would run hastily to the dark Lord's call.
However, if an ambushing company were to lack a good drumheller and be defeated, it could be disasterous for the morale back home. Thats why strong willed individuals like Mablung and Damrod and Faramir were chosen as captains.
Actually i think it was unlikely that Boromir was ever leader of such an attack. Before the Fords were lost there was little need of such forayes, since more damaging battle could be fought without the secrecy of sneaking over the river ( I wasss sssneaking!). Boromir and his bro had there dream the morning before the battle, the Fords fell and then Boromir probably left for Imladris soon after. I dont have the timeline on me right now so i cant check for sure.
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There long the golden leaves have grown, upon the branching years, while here beyond the sundering seas, now fall the Elven-tears...
but if of ships I now would sing, what ship would come to me, what ship would bear me ever back, across so wide a sea?
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