I've been slowly banging away at a small Grails app on the train to and from work, to teach myself Groovy the language and Grails the web framework. I already had a good familiarity with Java, Spring and Hibernate so it is mostly a case of learning what Groovy and Grails add on top of those. I've still got a long way to go, but I thought it worth jotting down some thoughts in case they help somebody else work their way into this particular world.
Overall, it's been fairly pleasant and I'm optimistic that it's probably as good a way to go about your average web app as any I've found before, and I've tried plenty over the past decade, including a few fairly obscure ones. I should point out that I don't believe in silver bullets any more. There are always going to be frustrations along the way when using any technology for a non-trivial project involving real-world customer requirements, but it's instructive to see just how many of those frustrations there are, and how hard they are to get past. I'm pleased to say that each time I've got a bit stuck with Grails I've been able to dig myself out fairly swiftly with the help of the existing documentation, other web resources, the #grails channel on freenode IRC and the grails-user mailing list. Furthermore, the principle of least surprise (POLS) is alive and well, meaning that when I hope that I'd find a particular feature to solve my problem du jour, it's usually there for me to find.
It's not all sunshine and roses though. For instance when I upgraded to Grails 1.3.3 my unit tests started failing with a strange and unhelpful stack trace emanating deep from within the guts of the plugin framework. Turns out this is a bug introduced in 1.3.3 that plenty of people have been caught out by. I've had to go back to 1.3.2 for now. It's a shade surprising and disappointing that a release could contain a bug like this, and that it's not been fixed and re-released yet. I worry that people trying Grails out for the first time with 1.3.3 will have a bad experience and give up early because of issues like this.
I had a struggle to find half decent tools. I've been a huge fan of Netbeans over the past several years and it claims to have great Groovy and Grails support, but I found it to be woeful I'm afraid. Common GSP tags completely confused the GSP editor (it claims the syntax is wrong) so I struggle to believe that those claiming it has this great support have actually tried developing a non-toy Grails app with it. I've settled on SpringSource Tool Suite (a bastardised Eclipse) which isn't bad - though as of this writing you definitely want to get the 2.3.3 M2 version for the latest Groovy and Grails support that's not yet in the stable release.