Does Racket use a DVCS? A git checkout involves making a copy of every historical version in addition to the current one, so their code is still being distributed. If a lawyer wanted to make trouble, they could argue that the repository as a whole is a single work and thus must remain on the GPL.
Each version presented by the VCS contains a copy of the GPL.
The GPL for Version 1 (example) would be presented if you checked it out and if you check out Version 2 it's now an Apache 2 license. The license in each case applies to the files in the VCS, a the GPL contains no special case for access to previous or future versions of the same file under it's license under the GPL license, neither does the Apache license and I doubt such a clause would hold water.
Yes, Racket uses Git. Which things are and aren't a derived work of other things is a complicated question which is, for example, the subject of a big lawsuit between Oracle and Google, and I won't pretend to give a final answer here. But we did follow the advice of our attorneys as part of the Software Freedom Conservancy (one of the big benefits of joining SFC is having such attorneys who know about free software copyright law).
IANAL, but pretty much no. GPL covers software that is linked against GPL software or containing any GPL software. Just having a GPLed file present, especially if it is in the past, does not affect anything not depending on the GPLed file. Products routinely ship together with GPLed software without falling under the GPL, as long as the non-GPL program does not depend on the GPL software, doesn't link against it or doesn't use any source under GPL.