I can’t believe I haven’t contributed to this list yet. I thought for sure I had, but… nope!
My first copies were technically pirated: The 1984 CBS premiere of Star Wars taped onto VHS, and then copies of Empire and Jedi taped off cable from a friend who had it (our family didn’t get cable until much later)
My second copies were… ALSO pirated: I rented the videos from a rental store, and used an old VCR to dub them.
My third copies were finally legally purchased: The Faces VHS set.
Fourth copies: The Widescreen VHS box set with the hologram cover (one of my first eBay purchases, too).
Fifth copies: The Widescreen SE box set
The Phantom Menace on Widescreen VHS
The Phantom Menace on DVD
Attack of the Clones on DVD
The 2004 DVD set
Revenge of the Sith on DVD
The "Complete Saga’ blu-ray set
The Force Awakens on blu-ray
Rogue One on blu-ray
The Last Jedi on blu-ray (Target exclusive)
Solo on blu-ray
The Rise of Skywalker on blu-ray (Target exclusive)