Although they are pretty slow right now, gemtools which is used with gemstone to interact with the always headless server is nice. you can use it to login and work with the smalltalk environment.

The stuff I'm using seaside for, is much easier to do when running on GLASS ( gemstone + seaside ) compared to running on squeak. I haven't used Cincom's web velocity which is also a Seaside environment, but it would be worth checking out as well.

The lack of docs is a little hard, but I've found the mailing list and irc channels very helpful ( even if you just lurk ). Is it a substitute for good documentation that exists outside the code and helps you ramp up? No. But it isn't the barren wilderness it would first appear to be.