I have been using Google Apps for my own business for several years now. Must say, have not needed to upgrade to paid (I have the free option) yet because it's just me and a handful of people so it's definitely not in the same leagues as your company.
As a software, I love the ability to manage the emails. I do not like email management and email servers at all that's putting it mildly and nicely. So going Apps is certainly the easiest, and even if I paid $50/year for it, I'd do it because there's just so many problems managing emails it's a full time job on its own.
I haven't managed enterprise email server before but have managed an email service (autoresponder, mailing list). Let's just say things can go to hell in a short period of time and cost you to sprout gray hairs instantly sorry for being so dramatic, email management and me is like oil and water we just don't get along so having someone host and manage it for me is a huge peace of mind. I believe it would be for many companies as well.
If you are concerned about Google as a company itself - I was told that Google Apps data is treated differently. In fact, you'll often find neat features in Gmail you won't get on Apps but that's OK with me. Also, sometimes not always, when Gmail goes down, Apps seems to work fine.
They say they have passed an independent 3rd party audit for security and privacy but - like everything else you sign up for, you can only take their word for it. So that part, it's entirely on your court.
sorry for being so dramatic, email management and me is like oil and water we just don't get along so having someone host and manage it for me is a huge peace of mind. I believe it would be for many companies as well.
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