I have now upgraded to a newer Pixelbook that has built-in support for 
Linux. After enabling the Linux container, these are the commands I used to 
install MLO (via wine):

#! /bin/bash
#
# repositories for wine & winetricks
curl -s https://dl.winehq.org/wine-builds/Release.key | sudo apt-key add -
sudo bash -c "echo deb https://dl.winehq.org/wine-builds/debian/ stretch 
main >/etc/apt/sources.list.d/wine.list"
sudo bash -c "echo deb http://ftp.de.debian.org/debian stretch main contrib 
>/etc/apt/sources.list.d/winetricks.list"
sudo dpkg --add-architecture i386
#
# now update the repositories
sudo apt-get update
#
# install wine
sudo apt-get --yes install --install-recommends winehq-stable
sudo apt-get --yes install winetricks
#
# now prepare everything for the installation of MyLifeOrganized
export WINEARCH=win32
export WINEPREFIX=$HOME/.wine
sommelier -X --scale=0.5 --dpi=160 winecfg # user has to manually click 
drives -> autodetect to set up the windows drives correctly, then save the 
new config
sommelier -X --scale=0.5 --dpi=160 sh /usr/bin/winetricks msxml6 # user has 
to manually click some things here
sommelier -X --scale=0.5 --dpi=160 sh /usr/bin/winetricks msxml4 # user has 
to manually click some things here
#
# install MyLifeOrganized
if [ -f MLO-Setup.exe ]; then
 sommelier -X --scale=0.5 --dpi=160 wine MLO-Setup.exe
 sommelier -X --scale=0.5 --dpi=160 wine "$WINEPREFIX/drive_c/Program 
Files/MyLifeOrganized.net/MLO/mlo.exe"
 #
 # now install a start script and desktop icon so MLO is available from the 
chromeos launcher
 sudo apt-get --yes install icoutils
 wrestool -x -t 14 $WINEPREFIX/drive_c/Program\ Files/MyLifeOrganized.net/
MLO/mlo.exe > $HOME/MyLifeOrganized/mlo.ico
 ( cd $HOME/MyLifeOrganized ; convert mlo.ico[0] mlo.png ; rm mlo.ico )
 cat >$HOME/MyLifeOrganized/start-mlo.sh << 'EOF'
#! /bin/bash
export WINEARCH=win32
export WINEPREFIX=$HOME/.wine
sommelier -X --scale=0.5 --dpi=160 wine "$WINEPREFIX/drive_c/Program 
Files/MyLifeOrganized.net/MLO/mlo.exe"
EOF
 cat >$HOME/MyLifeOrganized/mlo.desktop << EOF
[Desktop Entry]
Version=4.4.8
Type=Application
Terminal=false
Exec=$HOME/MyLifeOrganized/start-mlo.sh
Name=MLO (wine)
Icon=$HOME/MyLifeOrganized/mlo.ico
EOF
 chmod u+x $HOME/MyLifeOrganized/start-mlo.sh
 sudo ln -s /home/mhantsch/MyLifeOrganized/mlo.desktop /usr/share/
applications/mlo.desktop
fi
#
# success!
#
echo "All done. Your MLO setup is now complete."

Put that code into a file called something like 'setup-mlo.sh' and place it 
in the Linux files. Also, download the setup program for MLO and place it 
into Linux files as 'MLO-Setup.exe'. Then open a terminal and run the 
command:

bash setup-mlo.sh

When winecfg comes up, click on drives, then autodetect, then save the 
config.
On the other installers, you also have to click some continue and install 
buttons. It was pretty straightforward.
Note the use of sommelier in the scripts to make the resolution scale 
better on the Pixelbook's hi-res (hidpi) screen.

The script will also install a proper icon and lauch script for MLO, so you 
can start it directly from the ChromeOS launcher.

This was tested with MLO 4.4.8.

Enjoy!

Cheers
Max

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