I'm a close second to Moth3r on least spent through the years.
Purchased new when they were released. Made my first full-film audio rips from these. Eventually lost them in a flood in the early 90s, along with nearly everything I'd ever owned.
Purchased used about a year after it was released. Offered it to Bkev for free a few years ago. He ignored my PM, so I donated it to the store front of a shelter for abused women, where they sell items to raise money. I take stuff there regularly.
Purchased used in 2004. Looking around the internet to get it transferred to DVD eventually led me to this site. Still have it.
Purchased new in 2006. Got home with it, opened the package in the driveway, removed this disc, and threw everything else in the trash can. Only the disc went inside the house, to be stored in a generic single-disc case.
Anyway, that's it. If there is ever a proper release of the 1977 theatrical version of Star Wars, I'll buy it. However, since the NPR version has long since replaced the film for me, I'm not really concerned. I haven't watched the film in four years.