Can Squeak be started as a daemon process? If not, how would you 
suggest to configure the machine so each time it's rebooted, Squeak 
will be launched?

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On Debian you can use start-stop-daemon in rcX.d scripts to 
launch/shutdown programs that do not fork.

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Yeah.  Here's my startup script to run my local Swiki.  You'll need to 
tweak the paths, usernames, etc. but this should show how to do it. 
start-stop-daemon is great!

After installing this script in /etc/init.d, you need to cause it to 
get run.  I use file-rc, and so I edit /etc/runlevel.conf to 
accomplish this.  With the default setup, you have to create symbolic 
links in the /etc/rc?.d directories. ( update-rc.d lexswiki defaults )

Overall, there certainly are an annoying number of steps to getting 
something to start after every reboot, but it is all straightforward. 
Given start-stop-daemon, you can make Squeak auto-start at boot time 
much like you'd do so for any other Unix program (sendmail, apache, 
squid, whatever).

-Lex

#! /bin/sh # # lexswiki  Startup script for Lex's Swikis #

NAME=lexswiki DESC="Lex's Swikis" PIDFILE=/var/run/$NAME.pid 
SQUEAKVM=/usr/bin/squeakvm

SSDAEMON_ARGS="--pidfile $PIDFILE --exec $SQUEAKVM"

[ ! -f /etc/default/$NAME ] || . /etc/default/$NAME

[ -x $SQUEAKVM ] || exit 0

set -e

case "$1" in start) echo -n "Starting $DESC..." start-stop-daemon 
$SSDAEMON_ARGS --start --background --make-pidfile --chuid lex --chdir 
/home/lex/swiki -- -headless echo "" ;; stop) echo -n "Stopping 
$DESC..." start-stop-daemon $SSDAEMON_ARGS --stop rm -f $PIDFILE   # 
because start-stop-daemon doesn't do this echo "" ;; restart) $0 stop 
$0 start ;;

    *) echo "Usage: /etc/init.d/$NAME {start|stop|restart}" exit 3 ;; 
     esac

exit 0

You might want to have a look at Dan Bernstein's daemontools  
(http://cr.yp.to/daemontools.html). Once installed, daemontools 
monitors  processes defined under a /service directory, bringing them 
up  automatically on boot. The benefit over a simple init script is 
that  daemontools continues to monitor launched processes, 
resurrecting any  that die unexpectedly.

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+1 from me. We use it on the SqF box as well. The startup script is 
 'run'  and is simply something like:

#!/bin/sh setuidgid squeakuser squeak -headless foo.image

(setuidgid is a utility from daemontools that sets the uid&gid to that 
of  'squeakuser', then starts the rest of the command line).

A process will monitor this script, and as soon as it exits (because  
squeak dies) it will be restarted. Can't get it much simpler than that