It's been a while since I last installed a new Debian machine, but as
I recall, no, you shouldn't need to tediously pick and choose from all
those zillions of packages by hand. Worst case, you should be able to
pick some sort of "minimum necessary" package group during the initial
install, and then add whatever other packages you want later with
apt-get,
after the initial install. I believe the Debian
installer also include some sort of binning of packages into big
functional groups in the Red Hat style. But with apt-get that's not
really necessary.
If you already have one Debian machine with what you want installed,
you should be able to look at its list of installed packages and just
feed that to apt-get on the new machine if you like.
Of course,
FAI
is probably the "right" way to install machines, but I haven't looked
into that yet.