Feel free to post your known pitfalls when dealing with this animal. I just spent the better half of the last 2 weeks on the phone with both Microsoft & Blackberry support, fixing a nightmare install. The server came pre-installed by Dell to the client. The client didn't request us to assist with the install until after the his tech left the office and he started experiencing problems. The server was not patched with any updates/hotfixes/service packs etc before it was turned over to me. The configuration was SBS2k8 with Exchange 2007, BES Express 5.0.1, SQL 2005 Express, WSUS, Sharepoint, & Activesync. Bes was installed because one user had a blackberry device, Activesync was installed because one user had an I-Pad. I spent 3 days on the phone with microsoft just getting the automatic update feature to work. Once the updates were all current, BES stopped working. 3 days on the phone with BES support, I come to find out that 5.0.1 isn't supported on 2007 SP3. 48 hours later, and I still need to move the exchange db's to the D drive. The server is out of disk space. lol We tried to tell the customer that it would be cheaper to simply reinstall, but the customer insisted upon fixing it. If you are thinking about installing SBS, please think twice, and install 2008 Standard.
to build on what b166er has already said Firstly though SBS is designed to be simple. When we put in new servers we mainly install SBS servers for small to medium companies. We never have an issue with them, even 2008. If you'd have installed it from scratch yourself you may not have had so many problems. This other guy prob just went through the wizards clicking next, next not understanding them. This has then f%^ked up the server for when you go involved. I suspect your windows updates didn't work because of WSUS. By default 2008 SBS installs WSUS and configures the server to look at itself for updates. However you have to manually set up "Auto approval" rules for windows updates which again I suspect the previous tech didn't do. this would have meant every time your server tried to get windows updates it would report that non were available. BES is s**t, full stop and you should use a BIS service as b166er said. But really SBS is actually a very good product and it makes a lot of administrative tasks even easier to perform than on a standard server.