Those Box Set songs are tough ones most of the time due to the Diamond-Ring-theory.
Jon has said on numerous occasions that there have always been songs they went back to because they weren't deemed "ready" yet at one point or didn't fit the album's theme in the end (I remember at one point Jon saying that the KTF album essentially had been written around the track Diamond Ring, yet it didn't make the cut).
Miss Fourth of July was written in 1991, yet the recording we know sounds like it had been recorded later than that. Drive was written in 1991, but released in 1997 and maybe even reworked there. I'm still convinced that they did reconsider Starting All Over Again at some point because the Box Set version sounds like he has to strain his vocals considerably and is much more out of his comfort zone.
I think they revisited some of their song ideas while preparing for Crush, simply because they had no idea where in which direction they should go and the lack of coherence on the record shows that.
And (I may be the only one here) to me some of the material from the post-DA/pre-Crush vacuum sounds somewhat similar to some of the Crossroad/Open All Night songs.
All points provided for You Can Sleep While I Dream are definintely valid, so I have two theories about that one:
1. The original song sketch really is from around 1993/94 since the whole song structure and melody fit too well. However, Jon may have decided that it needed different lyrics and that songwriter team worked out new ones for that after having finished copying One of Us from Joan Osbourne.
In the end, the song wasn't the direction the band wanted to take and it went back into the vault and then onto the Box Set.
2. Jon trying to emulate Saturday Night. Last year, he said in a Q&A that his regret about These Days was that he didn't put Saturday Night on there and made it the first single. So he's always had a soft spot for that song and may have wanted to do a similar one for Crush, hence the chord progressions being so close.
Now we should blame Obie for not labeling anything properly and leaving us with so much stuff to figure out about it.