I manage a small office. I've been using Office 365 (a mix of E1 and E3 licenses for my users) for about a year now. Overall it's been very good.
One of my projects for this year is implementing Active Directory (we didn't already have Active Directory...or any windows servers, for that matter). I've read a bit about DirSync and heard some horror stories. Also, from what I've read, it looks like I've done things backwards, the way that DirSync was meant to work is to sync from on-premises AD to the cloud, not the other way around.
Is there anybody here who has done this and can tell me how this should go down? If I had to start over from scratch, re-create user accounts, migrate mailboxes and data, etc., it wouldn't be the end of the world. As I said, we are a small office, we're talking teens of users, not hundreds or thousands. But obviously if there were some way to make it happen with less manual work and little or no disruption, that would be preferable.
Also (somewhat) related: how would you recommend doing it licensing-wise? I was thinking I would just get one box running Server 2012 Essentials R2 and I would be set. What downsides would there be to this approach (other than the user and device count limits)?