I am considering helping an open-source gaming project with creating their setup file. The game is currently weights around 300 MB and is packaged in a zip file, playable st
On Linux, YoFrankie has been using Zero Install. That's LGPL and also supports checking for updates.
You can either let users install over the web, or run 0export to create a self-extracting archive. 300 MB is quite big... would it be useful to split it into several packages (so that e.g. updates to the core engine don't require users to re-download all the level data)? Zero Install can handle dependencies like that.
Some other options can be found in the Management & Distribution section on gnomefiles.