Installing wine I think not be big problem for you, you only need to copy your downloaded wine package from wine.budegetdedicated.com and type this command in your chroot console:
sudo dpkg -i wine-release-xxx.deb
And then, copy all your files in .wine directory to your livecd system. Put it with the directory in /etc/skel.
sudo cp .wine .work/etc/skel
When copying, make sure you are outside chroot environment and make sure the path is correct.
One thing before you copying your .wine directory is, you have finish installing the applications. And make sure, the applications tun and configure well. We can't installing windows application directly into livecd system, since it need GUI.
For your sake, keep wine in it default configuration, especially in wine ability to mimic certain version of windows os.
Good luck!

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