Create a simple working installer for the major OS's that includes a useful IDE, Database connectivity to least one major database and a fully functional web server. Once this is working get some people to write a standard library for date / time functions, file IO, formatting output etc.
Never underestimate how difficult it is for a new user to setup a working environment.
http://www.newartisans.com/blog/ready-lisp.html
It's Aquamacs combined with SBCL, some documentation, and some should-be-standard CL libraries. Double click and it immediately takes you into a REPL. Aquamacs recognizes most of the usual Mac key bindings, making the Emacs curve not quite so steep.
I've tried SBCL with the Eclipse plugin and it's been a huge PITA. IIRC, I couldn't get libraries to install when I finally gave up. It may have improved since, but I'm not sure. Of course the fact that many cool-sounding CL libraries had defunct websites and inaccessible CVS repos didn't exactly encourage me...
I'm just learning and my conclusion (by elimination :-)) is that for Windows the best is to use Emacs + SLIME + SBCL. There is an installation guide here: http://robert.zubek.net/blog/2008/04/09/sbcl-emacs-windows-v...
In the comments there are instructions to get ASDF working, that I haven't tried yet.
I've tried to avoid Emacs, but it seems impossible. Lisp in a Box has a lot of problems, ABLE has still too many bugs and Corman lacks GUI programming without which I can't justify the price. CUSP also has too many bugs. So I'm surrendering and looking at Emacs.
For the web server part, just use good old CGIs.
I started by writing a domain-specific crawler which extracted certain information from a bunch of sites. But the sites I was crawling changed their design mid way. So I then ended up writing a program in CL, to which I describe the data that the site has. E.g. Name-of-city is "Edinburgh", Address is '15 Market Place, ED12', First-Movie-name is 'Bend it like Beckham', First-showing-date is '15 Jan', First-showing-time is '14:20'. The program then produces a function which when give a page from this website extracts this information in the form of an alist so that it can be pushed into the database.
Funnily enough the my site which shows this data runs on django.
CL is the perfect language for those who consider that development is not a social activity, and luckily for you, there are a couple of niches where this remains a sustainable delusion. For now. Meanwhile, Clojure carries on the Lisp heritage in the branch of software development that's not going to get extinct soon.