Around 2004-2005, I tried a couple of times to watch the movies in numerical order, with the 2004 OT, just to see if it worked, and if I could see the OT in the context of the PT. It was... interesting. With a strong suspension of disbelief, supression of the history of the development of Star Wars, and a grandiose imagination, it is possible. However, I quickly learned that I preferred to watch each movie in context of itself, not in terms of its retcons: I watch Star Wars truly believing everything that Owen and Ben claim at face value. I watch Empire happy to see Luke and Leia make out because the love triangle is totally legitimate.

Since I no longer watch the 2004 versions at all (after having gotten the GOUT), the prequels have become a different story. Without the forcefed changes, the OT doesn't fit with it nearly as well. Granted, even with the forcefed changes, it's still pretty incongruous... a fault of the PT, not the OT. Ultimately, though, I don't really think about it. I still watch the PT on occasion and enjoy it for it what it is and occasionally hate it for what it is. And for the connections/allusions/foreshadowing to the OT that are made, I briefly try to make the connection without thinking about it too hard.

Eh, I guess what I'm trying to say is that, while watching the PT, I can manage to see the OT as the future of that. However, while watching the OT, it's much harder to see the prequels, exactly as they are, as being the past. It's a bit more of a stretch.