I think there's a bit of fanboi-ism that is keeping the LESS and SASS camps divided, since at first glance both languages seem pretty similar. Here's where I think the real differences start.
Both preprocessors come with some baggage… With LESS, it's the notion that Javascript running client-side can handle CSS processing (a bad idea). The road from there to a Node.js or Rhino set up isn't clearly defined. The SASS webpage, on the other hand, displays the three lines of code necessary to start watching SCSS right at the top of every page, and the Compass CLI provides "compass create ". However, SASS and Compass are saddled to Ruby.
What really needs to be built for both systems is a good PHP processor. I really hate to say it, but most of us web developers don't have the luxury of working without PHP.
SASS's PHP analog is phamlp, but the original Google hosted project hasn't been updated since September 2010. This has led to several splinter projects on github, with none gaining any real traction. Drupal's AdaptiveTheme has recently included SASS support using a PHP preprocessor. Since this is a pretty popular base theme, I'm hoping it leads to the development of a more solid PHP preprocessor. However, I'm really not sure about the level of Compass support any PHP analog provides… The Ruby version of Compass provides sprite generation, which I believe may be missing from all PHP implementations of the library.
LESS's PHP analog is lessphp. While it seems to be maintained and follows the original library pretty closely, both lessphp and phamlp suffer from a singular shared issue… both are just ports of the originals.
Of course, any server-side language is better than PHP, so I can understand why both preprocessors were written in Ruby and Javascript. This may lead to better hosting support for alternative server-side languages.
My $0.02.