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I will be starting to work as a 1099 independent contractor at the end of the month and I am looking for convenient software / website to help me manage tax returns (I am based in Brooklyn, NY), keep track of deductible business expenses and generate invoices

  • Erm.. Quicken? There are a ton of accounting applications out there. – Scott Jul 21 at 23:24
  • Quicken, QuickBooks, Sage, etc., etc. Try Googling. – joeqwerty Aug 7 at 2:48
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It depends on your needs. Our company experimented with quicken, and while we liked it, it was too limited. We sell and generally recommend our clients use two other products instead.

  1. If you expect to do recurring invoices while offline and selling physical products or in a state that needs to charge sales tax for services (or otherwise like advanced features) than we recommend and sell our clients QuickBooks Online for us at a discount.

1.2 If all the above apply except that you do not need to send invoices automatically while away from the computer or totally offline for certain days, QuickBooks Desktop is a one time fee and not monthly.

  1. We commonly and successfully setup users with Excel for this purpose. You can properly categorize expenses and income with this, and just use something like PayPal for sending the invoices if tight on money and just switch to something a little later.

With both options you can then plug in the categories into HRblock or TurboTax yourself, fill out the IRS form yourself, or bring the categories expenses and sales numbers to a local accountant who will file the taxes for you.

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