Make sure you back up your files first.
Try Ubuntu or Kubuntu, both distributions are for people like us
You can download an iso file and burn it on CD.
search for install instructions, so you wont get scary questions you have never heard of before (like: "Does your network support DHCP?")
For as far as I know, (k)Ubuntu has some basic questions at install, but no really technical questions. Dont know for sure.
Print the instructions you need!
Make a backup of your files
Then install (k)Ubuntu from CD.
As for wine: you can install it yourself after installing (k)Ubuntu.
Then you can install your windows programms in wine again. Put your backupfiles back and if there are no errors, you have a new distribution.
BUT MOST IMPORTANT:
Make sure you back up your files first.