MacOS – Setting Outlook.com contacts and calendar on OSX

Maybe you've already tried this but I'll suggest it anyway.

Check Groups

1. Open Contacts
2. Tap the arrow in the upper-left corner labelled Groups if it exists.
3. Ensure you have selected the right group of contacts.

Try Re-Sync

If you need to re-sync because the above did not work you could try this:

1. Open the Settings app
2. Open Accounts & Passwords (or the Mail section on older iOS).
3. Select the account causing problems. (Usually called Exchange.)
4. Turn Contacts off and tap ‘Delete From My iPhone’ when prompted.
5. Turn Contacts back on and tap ‘Sync’ when prompted.

I've never tried any of the Mac Server products. But AnandTech has a pretty good in-depth review of Mac OS X Lion Server. A few of the conclusions:

...server administrators will be happy to know that, in spite of its deeply cut price and consumer-friendly distribution method, Lion Sever stacks up favorably against Snow Leopard Server.

and

OS X Server is most useful in a handful of different scenarios: the first is that you have a small network that’s in need of a full-featured but easy-to-manage and simple-to-license server product. The second is that you’re managing a network of any size that used to be all-Windows, but hosts a growing number of Macs (this is often the case in education, for example) - OS X Server knows that it’s going to be finding its way into a lot of Windows houses, and as such it integrates fairly well with existing Active Directory setups. The last is that you have a bunch of iOS devices flooding your network and you have no idea what to do with them - iOS management may be Lion Server’s ace in the hole.

(emphasis mine) Seems to fit your intended usage pretty well.

About your other question:

Besides, and this is a bonus question, do you have some experience in using Lion server to manage centralized Xcode development? (we currently use our own MacBooks and we keep in sync using Git, I'd like to know for different approaches based on OSX Server).

Keep using git, use the OSX server as central repository (maybe consider buying GitHub Enterprise or using an free/open source alternative for managing your git interaction). Install a CI-tool (Jenkins or similar) on the server and use it to create automated builds. Should work quite nicely.