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(More customer reviews)IMPORTANT! Windows Server 2008 can be purchased in many different forms. Picking the correct kind of license for your needs is not easy--even Microsoft says so on their site. BEFORE you buy, stop by the Microsoft "How to Buy" site. Since I can't put links in Amazon reviews, here's how you find it:
Go to Microsoft's web site, from the Windows menu choose Windows Server. Next look in the bottom right corner for How to Buy & Deploy" and click on that.
I've worked with Server 2008 almost daily for a year and a half now, and even now that I've gotten to know it pretty well, I still find it to be a mixed bag. Microsoft deserves praise for their hard work at improving Security, but the core of their solution (User Account Control) evokes a chorus of boos from the Administrator, who now has to use three or more clicks for almost every action they take.
Then there's also the matter of IIS: Server 2008 is the first operating system to implement IIS 7.0, and this version is substantially different from the IIS 6.0 found in Server 2003. Gone is the metabase, gone is the interface, all to be replaced by an entirely new way of handling everything, top to bottom. It was nice of Microsoft to still leave an IIS 6.0 mode for backwards compatibility, but really if you're going to the lengths of moving up to 2008, sticking with IIS 6.0 for web application deployment is ignoring much of the point of upgrading a web application tier in the first place. Just as with the Security layer, the goal of the IIS redo is noble: make applications easier to manage and more portable than ever. The downside is the learning curve--you really need to toss out much of what you know and patiently spend some time digging around in the interface (and reading--I recommend the Server 2008 Administrator's Pocket Consultant) to get the hang of it. You'll also need to educate your developers a bit if you want to take true advantage of its portability: for example, new sections in the web.config are created to handle the new features in IIS. Much of what was in the Metabase is now integrated into the web.config to make it easier to move an application from one machine to another and not have to manually reconfigure everything.
There are other fringe benefits that don't always seem apparent. For example, while I still feel that file copies and disk performance are bafflingly slow (Server 2008 and Vista like to think about copying, tell you how long they think the copy will take, and then continually update that estimate as they perform the copy, in my opinion wasting a lot of time to do so), we have also seen massive improvements in larger operations: backing up and restoring the system is exponentially faster for a Server 2008 box than it is Server 2003. Reboots seem to be quicker. Applications have more than one choice for memory management: Integrated mode threads resources noticeably better for our web applications than the "Classic" Mode that is more backwards compatible. Support for virtualization in both Hyper-V and VMWare has for us been (mostly) hassle-free. With both Vista and Server 2008 comes a Power Shell (command-line interface) that is amazingly strong: you can seemingly do almost anything at all using only a command line, if that sort of thing floats your boat.
The only remaining thing keeping Server 2008 from receiving much acclaim ties back into the security tedium I mentioned earlier. Reading the Event Viewer now involves an ugly, boxy interface that doesn't easily lend itself to resizing windows or boxes. Modifying a config file isn't as easy as right-clicking the file and opening in Notepad: you have to manually run Notepad as Administrator, respond to the UAC prompts, then choose File-->Open and manually browse to the file. The same is true for Command Prompts: if you don't run them as Administrator, there's seriously very little that you can accomplish. You can't copy from another machine directly into the web root: you will need to place your files in another folder on Windows Server 2008 and then locally copy them forward. And for security reasons, you cannot easily register an Assembly on the box: where Server 2003 would let you copy/paste or drag/drop, now you have to place the assembly in another folder and use the command line to manually register/unregister the assembly. IIS doesn't always pick up handler mappings: sometimes what I see in my developer's web.config I have to then manually re-add in the IIS interface.
If you're thinking of upgrading your Server 2000 or Server 2003 to 2008, you will find youself with what is ultimately safer, more powerful...and more frustrating. At the time I am writing this (Feb. 2010), I'd suggest that Server 2008 is, like Vista, not as polished and user friendly as its newer cousins Windows 7 and Server 2008 R2. Server 2008 inserts a learning curve into its use and a lot of gateways that slow down simple tasks. One can see where Microsoft was going with the new model: it just doesn't make the transition very gracefully.
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