>> I think I have some perspective on this considering that Basecamp was 
>> built using Rails with a separate HTML/design guy and separate 
>> programmer. The way that we worked, the HTML-guy prepare a template 
>> with just HTML.
>
> I usually work the other way around: I make a first draft template, 
> and the designer
> enhance it. Maybe I should try your way as it lets the designer really 
> do what he
> wants without any limitations set by my limited imagination in HTML 
> layout! In fact, you've already proved it works....

I think this is key. You want unbounded creativity for as long as 
possible. And if you already chosen to implement something with 
checkboxes, it's really not that easy to go some other route entirely.
--
David Heinemeier Hansson,
http://www.rubyonrails.org/  -- Web-application framework for Ruby
http://www.instiki.org/      -- A No-Step-Three Wiki in Ruby
http://www.basecamphq.com/   -- Web-based Project Management
http://www.loudthinking.com/ -- Broadcasting Brain
http://www.nextangle.com/    -- Development & Consulting Services