“I'm wondering what is required as far as issuing a 1099. If I purchase "advertising" on an individual's website, and over the course of the year I pay them over $600, am I required to issue them a 1099?”--->It depends; You, as an individual that doesn’t own a company, can although you are under no obligation to do so unless you are running a business. If you filed them, the IRS would just file them for reference when the recipient filed his/her tax return. There would be no advantage to you, and probalby a bit of expense and certainly some hassle. In general, UNLESS you have your trade or business, you are NOT required to issue a 1099MISC to your vendor, an I.C. You do NOT even have to issue a 1099MISC to an individual. IN other words, if you are an individual( NOT business/trade), then you do NOT need to issue a 1099MISC to your vendor even though he is an I.C or trade/business. ALSO, you do not use 1099-MISC for personal payments to individuals. You need to issue a 1099MISC to your vendor, but only if the payments were in connection with your trade or business.
“How do I know what expenses I'm required to issue 1099's for?”----> As said above.
“I am starting a new business, and I have a tax lady but I won't be seeing her until March. I won't have any 1099's to issue for 2011 but I'm trying to educate myself for 2012.”--->Then, you MUST issue a 1099MISC to your vendor, an IC, the individual’s’ website( the individual is an IC), as long as you have your business. You do NOT issue the 1099-Misc to your vendor as long as your vendor formed his/her website business as S or C corp.BTW, an SMLLC, a sole proprietor not elected to be taxed as S or C corp is not necessarily a corporation, so you can issue the 1099MISC to the LLC.