If the timing is close together, we tend to try and release them at the same time. If there is expected to be a protracted delay (like, say one was going to be a month longer than the other for example), we have released them separately in the past.
We have no way to fully know what will occur here. The old-old gen (remember that was two console generations ago now) runs on a codebase that is quite far removed from what 1.4 will be. So, while the DR team has spent a lot of time on the transfers from 1.3 Era saves to 1.4 Era saves... there is no code sitting around from which to build nor really any save files to test 1.2 Era -> 1.4 Era, skipping the middle step.So, we suspect nothing will happen here and/or they just won't transfer properly.
Do note, however, that the transfer system does not actually remove or alter the original saves - so you will not lose those, they just won't be playable in 1.4. This is potentially something that can be explored later on if it is an area of huge community need - but this is the scenario for launch.
If you have a PS3 file you would like to send to us before launch, we would love to have it - then we can test and see what happens and get back to you (and everyone) - follow the link below to do so if you want.
SUBMIT YOUR PLAYSTATION SAVES AND INFORMATION HERE!
It shouldn't, no. I tested a lot using JM (which is a godsend for testing purposes), and achievements (in game and system level) appeared fine for me.