Outsourcing can be one of the best ways you can maximize your efforts and return on profits while minimizing the amount of time you need to work. Think about it, is it really worth it to spend an hour writing one article and then posting it on Digg, Reddit, Facebook and Twitter when you could spend that same hour having someone write 30 articles, and working with your team to design a couple new sites?
Sure, I know the second option will cost you money although probably a lot less than what you think but at the same time, if you're getting 10 times as much stuff done and are doubling or tripling your profits, it's kind of a no brainer, right?
After all, some of the biggest names in the internet marketing business attribute much of their success to having decided early on to outsource a lot of the time consuming grunt work.
Considering one of the best ways to become successful is to emulate the tactics used by people who are already successful, it seems outsourcing would be a great way to go.
My suggestion for when to outsource is right about the time you become cash-flow positive with the sites you already have. But, if you have the money upfront to hire someone to build your site, make it look nice and fill it with great content, by all means, outsource immediately.
If you want to start slow and gradually build into outsourcing, my recommendation is to do it as soon as it becomes financially possible. After all, why waste months or years growing your business on your own when you can get to the same point in a tenth of the time by outsourcing?