Don't worry too much about things that are hard-to-use in linux... But I guess that's coming from a person who finds it easy to install Slackware/Debian.
I'll be talking about distro's I have used.
Which are:
Mandrake
Red Hat
Debian
Slackware
Ice Pack Linux
Here goes:
#1 Installation
Mandrake: Very easy, it has a fancy X installer which is quite user-friendly. auto detected all my hardware and there were no problems after install.
Red Hat: Also very nice, although there are some things that I missed like alsa(which i need for my sound card and which is included in Mandrake and Ice Pack Linux) and automaticly adding my wind0ze partitions to /etc/fstab(which Ice Pack, Mandrake and Slackware do)
Debian: I used 2 floppies to boot up for a network installation. It has a text based installer and auto-detected all my hardware. You have to get over the fact that it is text-based, but other than that it's has a really nice installation. It missed alsa, though, but thats all.
Slackware: I find this one easier to install than debian although that's just me. It is pretty much the same as debian although I used CD-Installation so i can't comment on the Network installation.
Ice Pack Linux: Extremely easy, i'd say it can easily compete with distributions like Red-Hat and Mandrake. I'd recommend this one as a first time install.
#2 Booting Up(without tweaking anything after a previous session)
Boot Speed:
from fast to slow:
Debian
Slackware
Ice Pack
Red Hat
Mandrake
Starting X:
These distro's boot up X during the boot process:
Mandrake
Red Hat
Ice Pack
The other 2 are started up by typing "startx" in shell
#3 Window Managers
All of them have both Gnome and KDE. I'd recommend KDE for n00bs, and blackbox for people who want speed(not the drugs, smartass)
#4 Configuration
Mandrake: Does everything automaticly except configuring X. For that you have to know the video card and monitor brand. No biggie.
Red Hat: Same as above + the fact that some sound cards need ALSA to run. Which Red Hat does not have.
Ice Pack: Same as Mandrake + something about alsa: I tried letting it boot automaticly but it asks you to modprobe some stuff.
Debian: This is a bit harder. Pretty much the same with configuring X but you have to know the Monitor's Vertical and Horizontal ranges if you want to configure the monitor. And alsa. but installing alsa is no biggie as long as you follow the guide.
Slackware: Pretty much the same as Debian
#5 Packages Managment
Red Hat: Uses .rpm files, they are seen as the most simple way to install something in Linux.
Mandrake: .rpm
Ice Pack: .rpm
Debian: .deb
Slackware: uses basic tarballs(which means compiling). I was able to install rpm during the Installation, I haven't tried it yet.
#5 Distro's in order of most liked to least liked
Slackware
Debian(these 2 are pretty tied, but I don't want to be a hipocrit because right now i'm using slack and liking it alot)
Ice Pack
Red Hat
Mandrake
Throw questions at me.