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Well, if you put the logos in your root "logos" folder before you create your league/universe, then OOTP should look for matching team logos in the root "logos" folder and copy them to the location you're talking about. If you have already started your league, you would either need to copy over any team logos in your saved-game/news/html/images folder. I wouldn't just delete everything out, because as you said, there are more than just logos in there. Basically every image (player photos, logos) for your league will be in that folder (I think).
Unless someone else is aware of something, I think you may be stuck doing a manual copy/paste/rename/restart OOTP or manually importing logos/uniforms for each team from the Options & Ballpark screen for each team. I think the only time it happens automatically is during the initial creation of the league, but someone might be able to correct me on that.
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