Hi Chris thanks for the post!
Is STS 2.9.2 working better for you? There haven't been many changes to the Roo integration between 2.9.2 and 3.0.0, so I'm curious as to what might be different about your 2 setups, but as long as you're up and running now that's good.
I've been looking into why the Roo shell hangs upon project creation. It looks to be a deadlock generated within one of our dependent frameworks, so it hasn't been easy to fix, though I'm hoping we can fix it by upgrading our dependency. This problem usually occurs when recreating a deleted project, but we seem to have more problems in this area on Windows than on other platforms, so there may be another underlying cause. Also, the Roo shell will just not update itself until STS has completed its build cycle, which could give it the appearance that it is stalled. I think this has become a more serious issue in 3.0.0 over 2.9.2 because 3.0.0 appears to be a bit slower and startup takes longer.
STS-2607: Roo shell does not start after project creation
The red exclamation mark is another thing we've been looking into (bug posted below). The classpath settings get dynamically generated & updated, but the Maven project configuration isn't updated to compensate for the changes. We need a way to recognize the first change and then automate the second. You can workaround this by right-clicking your project and selecting Maven -> Update Project Configuration, and this will usually solve any red exclamation errors without you having to manually update your classpath settings.
STS-2539: Roo: src/main/java not configured as source folder when created
Thanks for the feedback!
Leo Dos Santos
Committer, SpringSource Tool Suite