Upgrading to advanced configuration, what happens?

We only have 20 people to manage and nearly the same number of computer, with little fluctuation (ca. 4 people/year and 2 computer/year).
So far it works fine for us by using one server (Mac OS X 10.5.6) in the workgroup configuration, but now all the 'computer stuff' has been deligated by my boss to me.
It takes too much time to configurate every computer one by one (who has access/ updates/ installation of programms/ etc.) and I plan to upgrade to the Advanced configuration. Sounds nice, but I'am not a professional IT person ('boss: You can manage the computers between your experiments').
If I do the upgrade, do I have to configurate every thing once again (file sharing, open directory, print services), or is it nearly as before, but every thing after the upgrade can become much more complicated?

I would most emphatically recommend that you get your boss to sign off on you having no liability nor culpability for any results of work he expects you to do "on the side".
People study and learn for years - and appropriately so ! - in order to accomplish this kind of work effectively and efficiently.
If you are learning and have a non-production environment to work with and potentially wipe & reinstall where need be, then by all means, go for it (start learning).
But otherwise your boss should accept that s/he is getting what they're paying for, and since it is nothing, they should be prepared for that.
It is neither technically nor professionally advisable to foist a task such as this on someone and expect the result(s) to be that of a trained professional in that field. The fundamental concern is the disconnect there, and the unacceptable risk this situation could put you in, either now or in the future.
To the matter at hand, I generally recommend strongly against an upgrade, as compared to a (verified good) backup, wipe and reinstall and configure from the outset as "Advanced."
For computer management, you will want to run your server as an Open Directory Master,
and as such, you must must must have verified working DNS lookup(s) for your server's FQDN, prior to proceeding with re-installing & reconfiguring it.

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Upgrading to advanced configuration, what happens?

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