[OT] Google or Office 365 for K-12 Messaging System? Any opinions appreciated

Google Talk? Via Google Apps

Gmail vs Outlook for email

I think he means messaging as in total communication (email, chat, even PBX/SIP integration possibly) and possibly even collaboration systems or an LMS. From a messaging standpoint you're going to get features very similar in both products and if you are already a big MS shop, you may get some value from Office 365 integration with offline MS Office products (although Google Docs is pretty darn good as well as well and they're making it really easy with Google Drive). Both companies are going head to head and pretty hard at each other in this war for cloud based enterprise communication / collaboration.

If it's a student population that you are going to give accounts to, it's more likely they're more familiar with how GMail and Google Apps works versus how Exchange/Outlook work, cutting down on possible support issues. But kids also learn technology fairly fast so it wouldn't be hard for them to pick it up either. Google certainly has the "cool" factor going. And possibly better mobile support since Android/iOS seems to work nicer with the protocols that GApps are using (IMAP, CalDAVm CardDAV, Jabber) and provide a host of regularly updated mobile app rather than Exchange/Lync on those platforms IMHO.

What's better for your org is entirely up to you. I assume a whole school district would need to do an extensive RFP process, and would need contacts with both companies to compete for the bid. Put together a committee that's empowered to prioritize importances of features, such as security, platform support (both mobile and desktop), ease of use/training for the population, migration and integration with current systems, compliance with local, state, and federal regulations such as HIPPA, ADA, FERPA, and other legal considerations, liability concerns, privacy concerns, etc. etc. etc. and over time you'll find the answer that works for your org.

I used to work in higher ed that went through this process (and it took nearly 2 years to decide on a product), and our experience with our original MS contact was not the best while Google wowed us from start to finish.

Great response, hkim; thanks. I'm not a part of the group that's doing the RFP/RFI and have just been a part of the discussion peripherally. I'm curious to hear other org's experiences and if they've been happy with their choice.

Personally I've used both as a consumer and in enterprise settings, but I'm no power user of either. It's really like comparing two different types of apples (excuse the pun), rather than apple and oranges, they're pretty similar in what they do, they just go about them slightly differently. My concerns as a technologist would be what level of support can you be promised in writing and what are the penalties are there if such support is not met. Both products work, they'll always be one or two off cases that you just throw your hands up and it's up to the big G or MS to fix, and as long as they lay out what that process looks like and you're happy with it, you're in the clear.