Okay, I'm going to give it a shot! (Cross my fingers; this is my first post.)
The top three rarest anime I've seen that I can remember right now are as follows:
Makaryudo - A single 25-minute OVA that came out in 1989 and sailed straight into my heart. It had a great seiyuu cast: Takayama Minami played the lead character, Yama. I suppose its one claim to fame is that it was (still is, for all I know) the favorite anime of the lead singer of a heavy metal band called "Danzig."
Majokko Club Yonin-gumi A Kuukan Karano Alien X - This was an OVA that teamed up Creamy Mami, Pelucia, Magical Emi, and Idol Pastel Yumi. I'm pretty sure this wasn't a doujin video. The title was what I found on IMDB, but I'm still thinking it's pretty rare.
Gall Force: The Revolution - I don't know if this one's rare or not. It came out in 1996, and I don't think it's been released in the States. The character designs look totally like Nadesico's and the seiyuu cast included Mitsuishi Kotono and Yokoyama Chisa. I only saw the first episode, but I would love to see the rest one day.
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