The first few years I actually had to file taxes I forced myself to go full oldschool and do it all on paper. It was a bit of a PIA but if you were careful it w

The first few years I actually had to file taxes I forced myself to go full oldschool and do it all on paper. It was a bit of a PIA but if you were careful it was really not all that bad - unless you made a proper mistake and had to fill out a whole new form. It also gave me a much better understanding about how all these different software manufacturers work behind the scenes however and I highly recommend everyone do it at least once. If you have a very complicated tax filing however with multi businesses or lots of assets/depreciation then totally use a nice piece of software. These days I am lucky enough I used to work for an accounting firm so a friend does my taxes for free using whatever fancy accounting software they use and they get me all kinds of small wins I would not have thought of myself. I have friends who have more complicated returns than myself and the money they spend on a decent CPA is peanuts compared to the amount they save - you would be surprised how much little additional investment it is to hire a real person vs just paying for TurboTax!