The secret to this is to use payment cards (Visa, etc.) or third party payment networks (PayPal, etc.) to pay vendors (contractors, etc.): you then don't need to send 1099-MISC, as the payment system will send a 1099-K instead, thanks to the new IRS section 6050W.
I always struggle towards the end of the year thinking back to what my expenses were. I then try to go through my bank accounts and determine what was actually a write off. There are so many stipulations to what a write off is that I'm constantly afraid of getting audited. My problem is two fold.
1. I need to track my business expenses during the year (there are many solutions and I'll be using one this year when I begin contracting work)
2. The bigger issue is I need a way to know if the thing I'm trying to claim an expense for, right now, is actually a business expense AND what specific stipulations exist on this type of expense.
If there is a simple way to accomplish problem #2 without going to a .gov or yahoo answers I'd gladly use the service. I feel like I could focus more on work and other parts of the business if I'm not always fearing I did something wrong with an expense (I know you can pay others to do this, but I don't yet have the volume on income for it).