Hello and welcome to the forum.The wiki has instructions to chroot:http://chakra-linux.org/wiki/index.php/ChrootOnce you're in, just do pacman -Syu to make sure the updates are completed successfully.
If you are missing /etc/pacman.conf there is something very wrong with your install. Without that file you should not be able to use pacman at all.Please make sure that you didn't just miss the file. If it's not there please share your /var/lib/pacman.log and /etc/chakra-release.If pacman.conf exists, just follow this wiki:http://chakra-linux.org/wiki/index.php/Wine
Hello and welcome to Chakra! To answer no4, no you don't need to overwrite anything with new versions. Chakra is a (half) rolling distribution, so a "sudo pacman -Syu" will always keep you updated with the latest packages.