If the squiggles touch end to end such that there are not supposed to be any pen lifts, then yes, the timeout could be a factor.
Here is how to edit the timeout setting. Download a fresh copy of the CLI API, and open pyaxidraw/axidraw.py in a text editor. (You can do this right on the Pi if you like.)
Find the line that says
On the line before that, add the following line:
Take care that the indentation should match the line above it.
This will disable the servo power timeout. You can also set it back to short,
ebb_serial.command(self.serial_port, 'SR,60000,1\r') will set it to one minute, or
ebb_serial.command(self.serial_port, 'SR,43200000,1\r') should set the timeout to 43,200,000 ms, or 12 hours.
After making the change to that file, use
pip install . as usual to install the software. You do not need to remove prior versions before installing the new one on top of it.