My taxes are still giving me fits. The tax people are saying I can contribute X amount into my Roth but the program is saying I can't. It sucks. I don't have an accountant so I can't just pickup the phone and ask questions. I've been writing back and forth to a rep from HR Block and their program and their rep are both saying something different. It's driving me nuts!
That does sound frustrating. I've used Turbo Tax for years and haven't really had any issues with it. A friend of mine uses the H&R Block software and one year he loaned it to me so I could do a comparison. I ran our taxes on both programs, and the results were very, very different. The H&R Block program got us a much smaller refund than Turbo-Tax did. Needless to say, I filed the return via Turbo Tax and haven't looked at another program since. I really would recommend it. Its an upfront cost (although depending on how you file, there is a free version available online) but includes a free state and free e-File.
The first year you use it, it will be more complex as you'll have to enter everything. But in subsequent years, as soon as you start a return it will ask if you want to transfer last year's return. When it does that, it imports a lot of the information - name, address, filing status, dependents, where you got W-2's from last year, what banks paid you interest last year, and so on. If you changed jobs, you just tell it "no I don't have that W-2 this year" and it will allow you to delete that employer and add a new one, but if not much has changed, many of the forms will be pre-filled and all you have to do is add in the current figures. It will even import directly from some institutions. If an employer has it set up to allow importing, you can import the whole W-2, and you can also import banking info. They're really made it so easy. They also have a forum where you can search for answers to your questions, or ask one of your own if you don't find anyone else has asked it already.