So I looked at the logs, and I see the following (irrelevant lines trimmed out):
WindowsLiveWriter,1.5624,None,00002,27-Oct-2008 01:11:28.932,"Starting Windows Live Writer Beta 14.0.5025.904",""
WindowsLiveWriter,1.5624,None,00012,27-Oct-2008 01:14:59.874,"Downloaded new cab file versioned 14.0.5027.923",""
WindowsLiveWriter,1.5624,None,00013,27-Oct-2008 01:14:59.874,"Downloaded configuration resources are not newer than the current version.",""
Now, it seems to me that 14.0.5027.923 would be newer than 14.0.5025.904, but the updater doesn't think so. Is it working properly?