Thanks to russs15's GTF website, I learned about my SW past...
The very first VHS tapes I ever owned were the OOT. My parents gave them to me when we got our first VHS recorder. I'm not sure what year that was, but I'm pretty sure that the tapes must have been the '87 re-release of SW, the '84 ESB and the '86 ROTJ. These disappeared, presumed stolen.
They were replaced with the '88 'All Time Greats' trilogy release. I used to love the 'All Time Greats' collection trailer at the beginning.
I forget what happened to these tapes, but I replaced them with the '91 widescreen trilogy, which I still have. I remember being very keen to get them for the widescreen picture. I also remember my parents being confused by why I thought it was so much better to have a thin letterbox picture than the full screen. Philistines...
I purchased the '95 'Faces' widescreen trilogy when it came out, which I also still have. I think I was swayed by the digital remastering and the 'last time ever' stuff.
Finally, I purchased the '97 SEs in the widescreen box set.
Out of all of these, I think the '91 set is my favourite. The '95 set, apparently, does not have the '20th Century Fox' fanfare opening on ESB and ROTJ. Instead it has the 'CBS FOX' logo and fanfare. Unfortunately, the '91 set has been my workhorse set and the '95 my time capsule. Those ole '91s are gettin' pretty fuzzy...
EDIT: Incidentally, the oldest VHS in my collection is now The Princess Bride, the fourth VHS I ever owned. I'm also particularly fond of my widescreen Blade Runner: The Director's Cut, which I bought as soon as I turned 15 (my parents were quite strict about certificating). It has a trailer for Full Metal Jacket before the film.