Microsoft made Office 2016 for Mac available for Office365 subscribers. Since Drew does not use Office365 we're not yet able to get Office 2016 for distribution. I've heard they will make it available to retail in September, so we'll definitely get it by then if not sooner, and would be able to begin distributing it to students shortly after it is available to us.
As far as OSX 10.10.4, we are reaching out to all faculty and staff users and upgrading them to 10.10.4 as soon as possible. For students we do in fact recommend you just go ahead and apply the upgrade from the App Store at this point. There were reports of versions of 10.10 before 10.10.4 having problems with wireless connectivity, but those were fixed in 10.10.4 by rolling back some changes they made in earlier 10.10 versions. Meanwhile 10.11 will be out in the fall, and we'll be tracking that as well.