I'm kinda in the same position, I've been running a business/website for 7 years and have to consider when to expand and mature the business.
I've tried to keep things simple. I don't have employees, but I could find things for them to do if I did. My accountant recommended I incorporate to save a few thousand a year on taxes, but it makes accountant much more complicated. I decide not too. I usually decide to keep things simple, private unless there is a really good reason. I don't hire outside, whether that's contractors or employees. Contractors are simpler than employees (There are legal issues here and questions about whether you can trust contract workers as much as someone you know and work with each day--can't give away the business's intellectual property to some guy in Tawain just to fix bugs now.)
Contractors not employees. No need for HR manager or legal consult, no ugly benefits issues. Doing it in-house, even better.
Sole prop not corp, No need for fancy AR/AP, accountants or legal services.
The area where I'm mostly likely to develop is in profitable areas. There are some sets of tasks that could generate income, that I just don't have time to do. This is where I want to look to further the business. Can I find a contractor, partner, or employee who can improve my ad sales, for example, earning more than all the costs to bring that person in.
If a hire some SEO guy, can he earn his keep. Is it easier just to hire a firm?
Should I hire someone to do some techincal infrastructure work. I'm no expert in various technical fields, but the business requires some expert designs and implementations so that the business can grow upon those technologies. Would the business be more profitable in the long run if I brought in some key experts. (hehe, "key experts"--one of the experts I was considering looking for is a PKI guy)
Just my two cents.