That's quite the screening though, isn't it? "Must be willing and able to take a 2-3 month salary loss"

I suppose it works out well for you, you will get only those that really want to work at Automattic and are willing do sacrifice for a chance, since they risk running a substantial loss if they aren't offered a position after doing a three month try-out. That is, for all areas where $25/hr is hard to impossible to live off of, especially for people with children, you end up either with those that are set up by previous engagements or are true believers.