Ogre lost a lot of them. If you buy a membership (which I recommend, he deserves the money and you get access to all dungeoncorp content), he mentions in scattered comments a few issues.
The old site used an old version of PHP or something that was being deprecated, so he was forced to update to the new site which came with many issues. To your question, MANY of his old videos are now completely lost. Hard drive failure or something, they're just straight up gone. If you notice, he doesn't have a single Hailey Young video up on the new site even though she was one of the most popular models. None of Emily Marilyn's really early stuff when she went by Molly Matthews. Etc.
The videos he has, he's been remastering as you noted. Some scenes I have in 480p, 720p, and 1080p as he's recut them over the years. For the scenes that are gone, pirate copies at the original released resolution are all that's left.
Finally, a few years back he noted new models just aren't bringing in the dough, doing so is a loss. So he's just slowly remastering the old stuff for re-release. I guess OF took too much business away. It's a damn shame, OF bans any really authentic, heavy BDSM. With Gord dead and Kink.com gone to shit, he's the only game in town. And he loves his girls ball-gagged, restrained, and often in shiny outfits. He's a top after my own heart.