Ugh. I hate doing taxes. Working through Guru offers many benefits, including the 1099 service. I do not have to do any 1099 paperwork and neither do my employers. Guru has my social security number but no one else needs it. I like it that way.
However, Guru does not do my taxes for me. (Sigh.) So, I prefer to use Turbo Tax. I could take it to a tax preparer, but the last time I was self-employed and had someone do my business taxes it cost $400. Turbo Tax Home and Business cost me $89 on sale, and it walks me through everything. It even gives me an option of setting up my own quarterly tax payments. You also get a step-by-step easy to understand walk through on your taxes, and it does all the calculating for you. As long as you put the numbers in correctly, it guarantees your taxes will be done right.
One year, I received another tax software in the mail for free and I thought I would use that (after all, it was free). It was so confusing, I think it was made for an accountant. I ended up purchasing Turbo Tax and using that instead.
Turbo Tax will automatically import from Quicken books, and most places will give you a discount if you buy the two together, but I haven't gotten around to getting that program yet. I think it would save time in the long run, though.
I do keep envelopes with all my important receipts throughout the year, then I go through and add everything up, check all my bank and credit card statements, and shred everything I don't need to keep. I e-file my federal taxes because it's free, but then I print a copy of everything, including a backup disk and shove it and my receipts into a large manila envelope with the year marked on the outside.
You should keep all your tax information for at least 10 years (so I've heard), but you might want to be safe and keep it indefinitely.