If you show more empathy you will have more success at getting people to move away from xp.
You will note I am trying to get them away with a solution.
As someone with technical knowledge, they are turning to you for advice.
If you sit there and empathise away, telling them not to worry, then you are sending them the wrong message. Its a lose-lose situation, they are not getting the correct advice and you are not helping your own cause when you have to then go tidy up the mess later.
As that article OSFO linked to said. Not spending money is not an option. Its simply a case of whether you spend it proactively now (i.e. by migrating to other OS) or you spend it later (i.e. clearing up the mess you've caused by being a clinger-on).