As to 3: Personally, I love gmail. But from a corporate perspective, you can still exert more control over exchange. This can be significant, especially for highly regulated businesses that need to worry about frequent e-discovery and may perhaps wish to take steps to limit what is sent.
As for Google Mail vs Exchange, my personal opinion is that Gmail is superior in evey way. If you need discovery, you can always shove email through your own gateway (running Postfix) and set it to store all emails it sends and receives. You could also use Postini which I think gives extra facilities like discovery. Might be a bit hacky for some organisations I suppose but I've never found Exchange that elegant or easy to manage.
The iPad I completely understand the appeal. It does not look like a computer. It looks like an Etch-a-Sketch. It's basically a handheld game.
I would love to read more about what your users want. It is interesting and educational.
I think they discover Dropbox via the iPad rather than via the PC. I don't tell them about it because it can be a bit confusing explaining how it works. But there is no confusion if they find out (for themselves) that it syncs their iPad to their PC and vice versa. Solves a very immediate problem in a hassle-free way.
I'm sure there are plenty of problems waiting to be solved in eduation. For example, multiple logins - to Moodle, Google Docs/Gmail, various other websites. Would love to see an app which sits in the tray and aggregates all these logins so a student can click to say "log me into everything" without ever typing a password except to get into Windows in the first place. (There's not much of a security issue with keeping all these logins in a central database since it's not that sort of login; just a way to play educational games or whatever.) Other things would include ways to get iPads out of the classroom. For example, some of our staff use them to film/photograph students playing sports so they can check their posture. For cricket, for example, it can be very difficult to prove to someone that their arm is bent at the point of delivery (which is a "no ball"). The iPad removes all and any doubt by showing the bowler a movie of his "action". Also, field science, etc - counting how many bugs are in a square meter of grassy ground, using image recognition to look up insects in a DB and say "That's a wood wasp" with a link to Wikipedia, etc.
You did ask ;) I'm sure you could find hundreds of things to do if you're looking for a project.
1. Cloud-based backup. It's insecure, bound to be hacked - never mind the encryption, teh haxxors can get around that stuff! So we're back to tapes and DVDs before you know it.
2. Virtual machines, but only if I make the mistake of telling them. It gives some people the willies for the same reason as (1) above, plus the supposed problems of a "shared" server. Also, if a server is outside our firewall they think it's less secure.
3. Google mail. They prefer Exchange for reasons which remain a mystery to me. I hate Exchange, love Google Mail and everything that comes with it. Even using Gmail via Outlook is mysteriously deficient for my colleagues.
4. Google Docs. Being able to collaborate on-line is not a very big benefit. The familiarity of MS Office is.
Things which do work:
1. iPads. This is the machine which will put me, an IT tech, out of work. Hasten the day.
2. Dropbox. Simple paradigm and works with the iPad.
3. All the clunky, difficult-to-manage, badly-designed software they've been using for years and have come to love in all their ugliness. It makes me weep.
The thing which will change this is the arrival of younger, more IT-literate people in the workplace. I have no problems at all with the under-30s; all the problems in the world with people older than that (not all of them but enough to be a permanent drag on progress). The simple fact is that these people will even shy away from something as superb as MailChimp's or Google's admin interfaces: too many buttons! They always get me to do it for them, and I will have a job in IT for as long as I want it.