Filing form 1099 in and of itself isn’t hard. It’s when dividends get into the picture that things get muddled. Any competent tax preparer can perform the task. When I file my taxes I always pay professional to do it for me. Even when I was filing the EZ form, they were able to point out and get me credits I didn’t know I was eligible for. The incredibly small amount I had to pay the preparer compared to the amount of my return I got back was well worth the expense.