This is so amazing! You managed to really nail not just the late 90's anime aesthetic, but the bootleg fansub aesthetic of the early 2000's. It feels like something you'd get off Limewire in 2003 labeled "BillClintonSexTapeHentai.mp4".
But I loved it not just because it was a funny parody of a bygone age, but the actual story itself is interesting even devoid of the parody elements and I really liked all the characters just as actual characters and would love to see a full on show of them.
Please make more! This premise and execution deserves full, 20 minute episodes!