Steve Jones - Editor (2/12/2010)

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1. Yes, no major issues I've seen reported here in 18 months since RTM.
2. The setup program for 2008 will do this. You can grab an eval, use a VM or separate instance to test
3. Yes and no. There was work done on the query optimizer, but will it help you? No idea. Depends on your code and what you're looking for. Lots of T-SQL enhancements are there, but you'd have to learn them and decide if they help your queries.
4. Nothing major. This was a new version, but it is, IMHO, SS2K5 with things bolted on for the most part. No core changes that are significant. Probably improvements to the SS2K5 engine, but not a major rewrite (like SS2K5 was for SS2K)
5. So hard to answer. I would say this. At this point SS2K5 is getting close to EOL. So in a year you'll be thinking of moving anyway to the next version, or a new version, to make sure you have support/patches. Or maybe not. If SS2K5 is stable for you, maybe you run it. I know plenty of people running SS2K still.

SQL Server 2008 R2 is coming out in May, but it will have a price increase, and most of the SS2K8 -> R2 changes are BI related. Data warehousing type changes. That may or may not matter. However if you're paying for an upgrade, it's essentially SS2K8 and you could plan on moving to that over the summer and then you'd have a long lifecycle of support for that product.

I tend not to upgrade if I don't need to, and typically have looked to skip versions since it's a lot of $$$

Brief Description
Download the Microsoft SQL Server 2008 Upgrade Advisor. Upgrade Advisor analyzes instances of SQL Server 2000 and SQL Server 2005 to help you prepare for upgrades to SQL Server 2008.