Photoshop and Illustrator are pretty much no-brainers at this point and honestly, I can't see much in the new versions that worth upgrading to, except that they're very OS X friendly at this point. If you are doing any kind of film/video work, then Photoshop CS has some useful new features to deal with the anamorphic aspects of DV and film.
Microsoft Office X is reasonably stable as a standalone product. We chose to go with very X instead of Office 2004 for our initial release because SP1 for Office 2004 wasn't release when we did our upgrade. There are however some problems with Office when it comes to integration with the Font Reserve Server software, which I'll touch on later.
That brings us to Extensis Font Reserve next, which offers the choice between the standalone Font Reserve and the newer Font Reserve Server system. The choice between these two is something that I think revolves around the size of your operation and need.
The standalone version is a fine product and we were using it for years with the only problem existing in that our font database had never been cleaned by anyone, resulting in a 200 megabyte, 10,000 font database that contained fonts we didn't own and contributed to instability. This allowed for our designers to use fonts that weren't ours, which is a big problem as workflow gets set up around these fonts. I think I would I recommend the standalone Font Reserve for use when you have less than ten people or so who need to access the server and don't have any immediate large-scale growth plans.
Now, the question comes in as to Server or not to Server. We ended up going with the server package for several reasons. The first of which wasn't cost, because it actually costs a bit more once you buy the server component (around $1000.) The decision mainly came about in a large part due to the aforementioned problem with the standalone version where anyone can introduce fonts in to the system and your font database gets unwieldy on each machine. Font Reserve Server does not keep fonts locally on the machine. Well, let me rephrase that. It does keep up to 500 of the last used fonts on the machine, but they don't really belong to that machine, they all belong to a central server which keeps the fonts stored in a searchable, extensible, SQL database that can back itself up.
Beyond all of this, we had a large group using our font database at the office. Between designers and editors, there were something like 70 people who needed at our font database. This was another reason we wanted to use the Server system, because if a designer introduces a new font in to the system (with IT permission, since we don't allow anyone to at fonts at will) it will then be available for everyone. When an editor opens up an InDesign document in InCopy, any font that the designer used will be there for them. I hope you can start to see the advantage in all of this and trust me, once the designers get over not being able to add whatever they want in to the font system, they see the advantage as well. There are some big things that will trip you up in the installation, but I'll get in to those shortly.