It's all about motivation. Every time they hack a reporter they get a ration coupon for a bottle of vodka.

It's not a pain to upgrade when you use patch management software like Ninite Pro. (unfortunately it isn't free, but it's not super duper expensive either) Don't forget also, that a lot of countries have data residency laws.. so depending on what kind of data your employees are working on, it may be illegal to use a cloud-based solution if it is hosted outside the country/trade block.