We bought our first Premium Annual Passes in 1995 and they were $199 each, no block outs, free preferred parking, various discounts. I think the regular annual pass was $99 and you could add parking for $25, but there were some blockout dates, and we were DINKs back then, lol.
The price went up, but they went back down in late 2001/2002, when we were buying 4 passes instead of 2 (youngest turned 2 in 2002), and were again $199 for a Premium pass. So 22 years ago we paid $796 for 4(!) Premium annual passes. By early 2011 we paid $459 per Premium pass. I know we didn’t have passes in 2014 and 2015 because the kids were way to busy with sports, and then got Sig+ passes in 2016.
Of course, Disney has added new lands and attractions since the days of those early passes. But I also think Disney became more popular. In the early 2000s it wasn’t all that busy.