I was a Swing developer (and loved it). Distributing Swing applications was never a major issue. The issue was that once the web hit, all my co-workers wanted to do web applications and convinced management web was where it was at.
I specifically mean such a simple thing that they have used the .jar file extension both for executable jars and plain archives of files.
If they had defined and promoted using .jxe as the file name extension for executable jars, there had been so much less confusion for the end users.
(Just like they have done with ear, war, rar, etc)
Also, the security considerations for java web start applications where rather strange, with ugly icons warning that you were running a java application etc, and much higher requirements for certificates and signed executable compared to just about everything else that you run on a computer.
If they had re-imaged the framework to use a "installation" and providing automatic updates, just like normal applications, they could have lowered the bar a little.
