In the old days, we had ifconfig, dhclient, APM, and things were simple.

First, came ACPI. This is not linux's fault, but boy did it make something simple as putting your laptop to sleep a real pain in the ass sometimes. I'm not sure how many hours I spent learning the acpi system, and getting it work on my thinkpad back before distros made it mostly work in most cases (but seriously APM, just worked, and ACPI was a pain in the ass)
I recently upgraded to a new laptop (thinkpad Z61p), on which I figured I'd put a brand new ubuntu feisty (now upgraded to gutsy), and I'm still running a recent kernel.org kernel instead of the vendor provided one. Maybe I'm getting punished for refusing to run gnome/KDE (I really tried, but gnome still sucks, and KDE still didn't quite do it, so I'm back to enlightenment), but simple things don't work:

• For some obscure reason, Fn+F4 calls acpi_fakekey, which then does nothing (apparently, it might still be talking to the wrong /dev/input/event0), instead of just simply calling the sleep script. Why so complicated? I mean this crap:
  

  cat /etc/acpi/sleepbtn.sh
  #!/bin/bash
  . /usr/share/acpi-support/key-constants
  #acpi_fakekey $KEY_SLEEP
  /etc/acpi/sleep.sh
  

  Seriously, WTF is acpi_fakekey, and why is there no documentation for it?
  
• tpb (thinkpad display) just worked, but was replaced by some complicated hotkey-setup package that does autodetection and still did the wrong thing for my laptop, and still doesn't do anything useful on my laptop with enlightenment (I had to hand re-install tpb, which ubuntu nicely made incompatible with hotkey-setup and ubuntu-desktop)
  
• pulseaudio just did not work due to a misbuild (/tmp/.esd vs /tmp/esd-uid), yielding broken sound laptop-wide
  
• but the best one is by far avahi, dhcdbd, and other network autoconfiguration stuff. Long are the days of simple ifplugd autoconfigure and /etc/network/interfaces is simply empty. Keeping up with all this stuff is starting to be really a mess, especially as documentation there is pretty light too.

I suppose that by the time all this is working, I'll still end up with a better config than what I can do on windows, but damn, it seems like it's getting unnecessarly hard...