These questions are worth asking. However, like you, I'm a bit biased too - except the opposite way. To me, some of the questions you raise (Do they have more

These questions are worth asking. However, like you, I'm a bit biased too - except the opposite way. To me, some of the questions you raise (Do they have more crashes? [..] More problems with program compatibility?) are points I would traditionally associate with Windows rather than with Linux. Is it harder to train people to use Linux? is an interesting question. I think if people are already used to working with MS products staying with these products should provide an advantage it terms of training. However, I would expect a significant portion of the staff to use only a minimal feature set available in their setup, typically writing letters, etc. For them, I wouldn't expect the transition from MS Office to an open source office suite any harder than, say, the transition from traditional MS Office to the ribbon-based interface. Is Linux as easy to use, or are there inefficiencies? -- The whole "this year is the year of Linux on the desktop" joke will probably never get old, but I think everyone has to admit that Linux has come a long way in the last 15 years. For your average user, I would say there aren't any major differences between a Linux desktop and that of a commercial vendor, once the system has been set up. Of course, that still leaves the question whether Linux systems are set up as efficiently as Windows systems... I personally think that MS Office at least looks way more polished than any of the open source alternatives, and I would expect it to be a good deal ahead of the latters in application as well. But I can't say for sure because I've used Open-/LibreOffice exclusively for many years now. It's totally fine for whatever I want to do with it, and I would bet that it is absolutely sufficient for 90% of the use cases an average admin person has. So all in all MS products might still be a (good) notch ahead in terms of product quality, but I think that advantage is somewhat neglectable because Linux alternatives have certainly matured enough for the particular use case of a city administration.