I feel your pain, and know what you are taking about. Hard to find someone who will not ruin your reputation, do things as you need them done, and most importantly stay motivated.
Money is powerful for the right person, but not everyone. Same going for the freedom of working in your undies. Let's face it, unless you are a disaplined individual, and can work from home, keep your hours, do your work, and be successful they are not a good fit. Some people need an office, that environment, out of their house, and someone with a foot in their ass to work. Unfortunate, but some just can't work from home, and waste all their time watching talk shows, or whatever is on and get little done.
I'd say for someone in your position, you need to sit and think about what your next 1, 2, 5, 10 year plan is. If you want to stay how things are with no office, you will need to work on a better business model, and chain of command, new people whatever. But if you are planning to grow, and know in your heart of hearts that you will eventually have to bring on more people, or it just will not function without taking the step. You had better just make it and get it behind you.
Honestly in the internet game, I would never outsource anything critical. Only mundaine tasks. Not sales. Not trade secret, seo or that kinda stuff. All depending on what all you are into with various projects. Some people can outsource, and make their coin. But some can't easily do it because of what they deal with in the industry.
My main suggestion would be work out your 3-5 year game plan, where you want to be, and if it's inevitable, just take the plunge.
