Finally got it working, thanks Tim! I had
export CPPFLAGS="-D_WIN32_WINNT=0x0601"
and --with-default-win32-winnt=0x0601
specified pretty much everywhere, but somehow this time around everything must've aligned and it worked, I produced a 3.65.0 binary with updates disabled that works on Windows 7.
Hopefully I'll be able to track upstream more easily if needed, but if Windows 7 support does become more elusive in the future, at least I won't be nagged about updating to something that doesn't work anyways.
The other major change still being I had to extend the last bit of the symbol stripping to:
$TARGET_HOST-strip data/dlls/*.dll || $TARGET_HOST-strip data/dlls_gui/*.dll
Perhaps you may want to update the cross compiling instructions to include the new directory?
How to properly disable updates and purge update cache?
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