nobody seems to be able to tell me what will be in 4.x, how important the new features will be, or when it will be out.
I would try emailing the AOLserver list with that question. My opinion is that it would be easier to maintain a native Windows branch from the early AOLserver 4 beta. Back porting bug fixes and new modules would be easier, and my experience has been that the 4 beta is more stable on Windows than the recent 3.x versions. My OpenACS 4.5 Win32 box is now http://empoweringminds.mle.ie/ so the installation doc I was working on is at http://empoweringminds.mle.ie/documents/one-doc?id=1.
In terms of making installations easier, I would like to create an MSI installer for the work that I've done. I will be using PerlMSI, which is part of ActiveState's Perl Dev Kit. Someone could do the same thing for a native PostgreSQL port, but I'm not volunteering. 😊 PostgreSQL on Cygwin already installs easily. AOLserver 3.x did have an installer, but since you had to patch the sources to make OpenACS work anyway it wasn't very useful.