The biggest problem I have with outsourcing housecleaning is that it is not only fairly expensive, but also very hard to find someone who does a good job.

We currently pay $90 every two weeks for a cleaner who comes and does about 2-3 hours worth of work. It is 2-3 hours worth of work that my wife or I could do about as fast if we chose to, and either one of us would generally do as good or better a job.

It's still probably worth it, because most of the time we didn't have a cleaner, we didn't choose to do it, even though it made us happier to have a cleaner house. We absolutely limit their tasks to the things we are less likely to do regularly, or are physically hard on our bodies (floors, showers, toilet -- both of us have back problems). Overall the house is cleaner, and in fact, we are motivated to do certain things (pick up, organize, clear dishes in drainer, etc.) in order to have the house ready for the cleaner.

I think the point at which it makes sense to outsource this is when you are making around $30-40 per hour for your time.