So I went ahead and cleared up the idea I had for this. To give more fairness and openness, decided to run this as a competition.
Most of the details are in the Pledgie here , but just to clarify:
Designers that want to participate, need to create a homepage image mockup of the website. These mockups are going to be exposed to everybody and a open poll is going to be held.
The mockup with most votes and that share the idea of the RubyInstaller project and guidelines is going to be awarded with the total money of the pledgie.
Money is going to be send over Paypal when HTML and CSS elements are shared publicly (GitHub or any type of code repository).
Designers will remain the copyright holders of the design and credits will be displayed in the website with permission of usage for RubyInstaller project.
I believe this is fair, and also can let people’s mind fly, so go ahead, mock something that can fit these needs and add those to the following wiki page at GitHub:
Website Contest – RubyInstaller
Once again, if you want to contribute with some money, please use the badge at the bottom of the page or this one:
And for those Linux and Mac users that want to contribute, you can do it anonymously 
Good luck everybody!
[...] Laverna, a significant contributor to Ruby efforts on the Windows platform, is looking for donations to help the Ruby One Click Installer get a new Web site. Luis does a great deal of work for the [...]
Is there a deadline?
Yes Ben, completely forgot to mention.
Campaign end July 19, 2009. My idea is do the poll June 19, 2009, but maybe it could extend a bit.
Ideally, the sooner, the better
RubyInstaller: designs and deadline details…
So, guess what? There are already 3 designers running for the pledgie prize collected for One-Click Installer new home!
Check those over there:
http://wiki.github.com/oneclick/rubyinstaller/website-contest
This is excellent news. Thank you guys for…