If you’ve never done your taxes with software, I don’t know why you’ve been waiting. I’ve been doing my taxes on the computer since the early days of DOS (remember DOS?) with a program I downloaded from a dial-up BBS (Before the Internet, kiddies), called AmTax.
Fast forward to 2020, and I’ll be doing my taxes with Turbo-Tax as I have for the last 30 years or so. It’s fast, easy, and very hard to make a mistake. And the reason I like buying the software each year, rather than the ‘free’ version, is, it remembers everything, making data entry a lot easier. And so you know, if you do much beyond basic forms, the free version isn’t free anymore.
There are several tax programs, both online and as software, that are perfectly fine, and I have used a few. But when I started accumulating data that needed tracking year over year, such as passive gains and losses, I settled on Turbo Tax and never looked back. Any major tax software will do this, but you need to stick with the same company to track historical data.
You can buy Turbo Tax as physical software, or buy it online. If like me, you find the best price as software, in my case at Costco, you can still download it. My current laptop doesn’t have a CD drive, so I had no choice. If you buy it online as downloadable software, follow the instructions from the vendor on getting your local copy. At that point, the rest of the instructions should be the same.
Also, for each version, there is a desktop version, either physical software or downloadable, and an online version. Compare versions, both online and desktop from various vendors to see where you get the best deal. For me, Costco had the best price I could find, including the discount offered me by Intuit.
One significant difference between the desktop versions and the online versions are the forms included. Intuit’s marketing will usually give you the impression you need a higher level of the software than you do. But the desktop versions have all of the forms available; the higher levels offer more help. I have rarely felt the need to make use of their support, but your results may vary. Don’t get scared by that, however. The amount of help you get just filling out the form is enormous.