Ask HN: How and When to Outsource

I do front end web design and web development. One day I would like to make apps but I am spending more and more time managing past clients, helping them make changes to their site as their content evolves. Even in addition to having a CMS. I would like to outsource some of this but I have no idea how to start. So HN, - when have you resulted to outsourcing / delegation? - How did you get started? - How did you devise a system for it? Thank you all!