Hi Amy,
This is a struggle many business owners deal with. I'm going to answer your actual question first since no one else did, then debate the wisdom!
Hiring your First Employee
Recruiting: You need to find the right person. While doing your interviewing, be careful not to stumble over the protected classes discrimination issue ( http://en.wikipedia.org/wiki/Protected_class ). That means, you can't talk about things like race, religion, family, disability etc. Make sure you have a clear list of requirements and a grading scale. This should sound familiar as a landlord, since it is pretty close to the issues we face from HUD. Key think is to really figure out what the right blend of skills are that cover the majority of your needs.
Payroll & Taxes: You can't just cut someone a check. You have to withhold the right amount of money for things like social security, medicare, local and federal taxes. You will also need to pay the employer portion on top. You can either do this yourself (suck) or pay someone, either a bookkeeper or a specialized payroll provider. I pay about $150 per month for 7 employees.
Benefits: Full time, part time, salary, except, overtime... all things you need to figure out as the rules are different for each approach. For example, if you were to use an hourly employee, then you need to keep track of their time, and if they work more than 8 hours in a day, or 40 in a week, you owe them overtime. There are also laws about the type of leave / sick pay people get, as well as other forms of benefits.
Legal / Contract: Once you have the right person, you write them an offer letter. It will detail their job requirements and their compensation. Typically you also have some kind of company policy / handbook, that defines the rules of their employment. Things like, lunch breaks, or vacation policy, or how much money they can spend without written authorization.
Compliance: The laws around 1099s are vague, but ultimately simple. You just need to be sure they qualify using the IRS 20 guidelines. Compliance around employees is greater. People like OSHA now pay attention. Local government agencies want to collect paperwork and funding for employees: business license, office inspection are things we deal with.
Insurance: Workers comp is good. You will also need general liability. You might even want to consider E&O depending on the tasks they handle. If they drive, then make sure their vehicle is covered in case they hit someone while on the clock. You should probably also make sure they can make their repairs / fixes without a contractors license, or find someone who carries one.
1099s, and Why I think you Should Kiss More Frogs
Finding a good employee has been no easier than finding a good contractor. To put it in perspective, I have 33 part time contractors on my team. We added 11 new ones in 2014. 1 out of 5 made it long term. I think our best year ever was 1 / 3. You have to build good filtering systems, lean heavily on referrals, and always be recruiting. I just had a new handiman make some repairs to my home last that I could have done myself. It was a good opportunity to test someone. Sadly, he failed. Work was good, but he was stupid slow and was not organized in a way that would work unsupervised. I typically keep 2-3 handymen who passed on roster and try 3-5 a year on new tasks to keep my list current.
I could be wrong, but my experience having both is that employment won't solve this for you, but as @Paul Ewing eloquently stated, it will offer you a whole new family of migraines.
I did a talk in 2010 to a conference of business owners on how to find and manage independent contractors (Freelancers are slutty, but so are you: Strategies for the successful management of independent contractors). Maybe something in the slides might be of help: http://www.slideshare.net/shanepearlman/freelancer...