Well, the big problem with configure/gmake is that it is total overkill for the problem we're trying to solve and not terribly user friendly, either.
Unless you're thinking of writing umbrella scripts to configure and make all the C pieces (AOLserver etc).
OpenACS itself has only one configuration choice that's of interest: which DB to use. Currently we depend on the user configuring their nsd.tcl init script properly, we could have an umbrella tclsh (or whatever) script ask for which database, user names, passwords etc and write the script for the user.
Other than that, though ... is there anything that's hard OTHER THAN installing AOLserver, PG or Oracle, ImageMagick blah blah blah?
I think we should look at defining the problem space a bit more tightly here. If our goal is to lower the hassle factor for people who want to try it out, do we really need to worry about debian people? Anyone running Debian is going to know how to install debian packages.
The person running RH or Mandrake or Fedora from an end-user CD set is much more likely to need help. Maybe we should concentrate on one platform like this first? Our resources are limited...
And for anyone with a spare machine sitting around, the Knoppix CD approach is a great one, I was only partly joking when I said that it would be cheaper to just ship folks a $200 PC than to try to support every Unix variant out there.