Yes – it does indeed work. After a good bit of poking around in the innards of the new ProjectAggregator, I managed to get a version of Ruby In Steel to run well under Orcas (aka Visual Studio 2008).
A few weeks ago I downloaded the new Visual Studio 2008 Beta 1 and its associated SDK - a hefty 7 GB or so. Even with a decent broadband link it took some time. Things did not go smoothly however. The main problem was with the new ProjectAggregator which is supplied as an integral part of Visual Studio instead of the current hack of providing a separate DLL which has to be installed before the main package.
The trouble seemed to center around finding a GUID for the COM interface for the aggregator – it wasn’t in the right place. After a bit of head-scratching I just added a registry entry in what looked like a likely spot and it worked! It is a beta after all, so I’m not complaining.

So what’s different? Well, not a lot as far as I can see. Yes, there’s LINQ but that doesn’t affect Ruby very much - though, as a matter of fact, I do have a few ideas for database IntelliSense. And there’s a new HTML Editor. The current HTML Editor in VS 2005 is OK – but it’s not great. I’m particularly interested the new HTML Editor because the new Visual Rails Workbench (due in Ruby In Steel 1.2) works quite closely with the standard HTML designer (not the Web browser control, btw – that’s something quite different). The problem with the current Visual Studio HTML designer is that it’s a closed world. There’s little or no documentation on how to use it, the interfaces are not documented. In general, it’s a real PITA to work with.
So I’m hoping that the new HTML designer will be a bit more amenable to tweaking – ideally, I’d like it to be like the Visual studio Core Editor which is the basis for much of the RiS functionality. However, there’s no documentation on the new HTML designer yet (and I’m not holding my breath). But there’s one really nice feature to look forward to – JavaScript IntelliSense (see HERE).
For my point of view, VS 2008 is much less of a jump from VS 2005 than moving from VS 2003 to VS 2005. There are some nice new features, and much better licensing conditions on building applications with VS 2008. Fundamentally there doesn’t seem to be much work to do in moving from VS 2005 to VS 2008. Hopefully, we should be in a position to trial some beta versions of RiS with VS 2008 beta 2. Though, this does depend very much on the VS 2008 SDK.