Internet cafes and wireless signals are easy to find in traveler areas - and really are cheap - $1 an hour or less. You hit it on the head though, expect most of the hardware to be pretty crusty.
Unless you plan on doing a lot of writing or work from remote, carrying a laptop around can get pretty cumbersome. It changes your trip actually. Personally, I didn't carry a laptop on my first trip and it was a good thing, I didn't have to worry about it constantly getting wet, abused, or stolen.
I do recommend carrying your own headset for Skype
to make calls, not all the cafes have a working one plus maybe a large USB thumb drive for backing up files and pictures. If you want to upload photos, bring a card reader or USB cable to get your photos on the internet cafe computers.
IPOD - hell yes. You will go mad on long bus rides without it.
I carry a USB charger and just charge it in the cafes when I use the computers...or you can get a power adapter that will work for multiple countries...the plugs are different everywhere.
Others' opinions might differ, this is just the way that works best for me.