I ducked out of work to buy my first copy of Privateer shortly after it was delivered to the local Egghead (according to the receipt in the box, I bought it at 12:34 pm on 10/27/93).
Yes, that first play-through was probably the best. To this day, Privateer remains my all-around favorite pc game. Played it off-and-on for months and then bought RF and continued to do the same.
The definitve edition was, of course, not the first one with its 6 3.5 floppies. That would be the full-voiced CD-ROM edition, which I bought on 7/1/94. I subsequently bought two additional copies of the game: the EA CD-ROM classics edition (to have a backup copy), and the EA CD-ROM Classics Gold Edition (which included a tailored autoexec/config.sys for Win95 DOS boot-up).
By the time I got to Win98 SE days, it was getting tough to run Privateer. Had to use a special mouse driver ("Mickey Mouse") which loaded high. Only way to squeeze the necessary mem to get everything needed to load the game up. Now DosBox has pretty much made all the old games playable again.
What's weird is that I thought the original Privateer came with an optional speech pack.....but I'm just not finding it in the old game closet. Maybe I'm confusing it with WC2.