The track titles alone have so much personality it's wild. OreImo Portable's PSP soundtrack does this thing where every song name is stylized differently and somehow that chaotic energy carries through to the actual music.
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"SOFT BREEZEEEEE" with all those E's is exactly as laid-back and drawn-out as it sounds. "AKIHABARA,CHIYODA-KU" drops you right into electric town with this bustling, energetic arrangement that nails the atmosphere. Then "downpour" hits and everything gets quiet and reflective.
The PSP's audio limitations actually give the whole thing this slightly compressed, intimate quality that fits a portable visual novel perfectly. If you played the PS3 version but skipped the PSP entry, this soundtrack has its own thing going on and it's worth hearing.