What about helping him to know where he stands? (Score 1)

The fisrt thing I would do would be to ask how much time and effort did he spend on windows and how much time he was willing to give to Kubuntu. Second I would ask him to put things into perspective meaning that windows is not wihtout limitations, just he happen to have bought a system that was "built to be compatible with windows" and he is trying to use it with something else. Third I would ask, high level what he meant by "not working" as lots of other people have a different perception of it; Normally it will go down to hardware support or compatibility with office or his custom windows application he depends upon. 1) Harware: it means mostly video dirivers, suggest a cheap Nvidia card or a wifi card unsupported 2) Office Cxoffice or Vmware 3) custom application vmware if he sees this as complicated ask him to list the problems he has with windows, probably he has many and they are causing him lots of time wasted an worries. He has probably never put them all together so he does not realize how many he has. It helps to put the problems he is facing with linux into perpective.