I wonder how the quality of their Linux systems compares to an equivalent Windows set-up. Do they have more crashes? Is it harder to train people to use Linux? More problems with program compatibility? Is Linux as easy to use, or are there inefficiencies? Saving money is one thing, but time = money so if using Linux wastes time then is it really an advantage?
Maybe I'm just looking for problems. I'm a bit biased; I happen to think it's a matter of self-respect to spring for quality software instead of just always using the cheapest option. It's one reason why I would prefer to use MS Office over OpenOffice, because Office 2010 is a quality app with a polished interface whereas OpenOffice and its variants look to me pretty much like crap on a stick. I also like the idea of rewarding quality software and promoting more of its kind with your money. We should all be happy when smart people making good products get paychecks.
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.
I found it felt very natural to use Linux Mint coming from Windows 7. In fact I even thought Mint is more intuitive than Windows 7. I can't say I had the same experience with Ubuntu's Unity, though.
Also I need to try out Zorin OS (zorin-os.com) one of these days. It looks like they made it so it works as much as possible like Windows 7, so it should be even easier for people switching from Windows.
Maybe I'm just looking for problems. I'm a bit biased; I happen to think it's a matter of self-respect to spring for quality software instead of just always using the cheapest option. It's one reason why I would prefer to use MS Office over OpenOffice, because Office 2010 is a quality app with a polished interface whereas OpenOffice and its variants look to me pretty much like crap on a stick. I also like the idea of rewarding quality software and promoting more of its kind with your money. We should all be happy when smart people making good products get paychecks.