I'm not a java guy either but here is an answer from the java guy who told me about the issue:
The problem is related with heap space, which is handled by the non standard variables -Xms (minimum heap space) and -Xmx (maximum heap space).
Each JVM has an initial value for the heap space for each OS (and each Vendor). So, something that works on one machine with a JVM won't necessarily work on another.
It seems that only the windows script (js.bat) has the -Xmx option set. The -Xss option is the stack size and not related with the heap space. Without the -Xmx option on the linux/Mac script there is no guarantee that it will work on the broad range of OSes and JVM vendors. Adding only the -Xmx option doesn't seem to have any big implications, beside that it requires enough RAM to perform.
I can submit a patch for the js non-windows script if you like
We are java guys over here. Basically, compiling Less files take a LOT of memory, especially if they @import other less files. We are doing pretty much the same thing you are doing with the main.less that imports other less files and is itself imported. We have had to raise our -Xmx setting (max memory you allow the java process to take) several times as we add more components each with a less file to our app. It is now at -Xmx1500m which is a ridiculous amount, but hey, it works, and on our developer machines there is still RAM to spare so we're ok for the moment.
We are also very much looking forward to running in Node... also because our Less file minifying is now taking almost 2 minutes, when it used to take 10 seconds...
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