Thank you for any help!
Can I tell you something which is much, muuuuuuuuch more significant than the $25 or so you're contemplating spending on tax preparation software? It's highly likely that you're running a sole proprietorship (Schedule C). I am not sure from your phrasing that you are aware that you are doing something which can be categorized as a sole proprietorship. It is to your advantage to characterize what you are doing as a sole proprietorship given some plausible assumptions about what your cost structure is, because you will be able to deduct all expenses reasonably required to run the business from the revenue of the business (the number shown on your 1099-MISC) prior to paying taxes on the profits only. What the IRS considers "reasonable and necessary" is not what most natural humans would consider reasonable and necessary.
If you do not feel like reading an awful lot in the next month, bringing every receipt and credit card statement you have from the last year to neighborhood accountant will cost you a few hundred bucks and save you, plausible, 10X that in taxes. This is the bread and butter for lots of small accountants and tax-preparation shops, and they're reasonably good at it. WSJ? Deductible, always, 100%. Phone bill? Guesstimate how much of it was for business? 60%? Good enough; let's find all twelve of them. Do you have any other phones? Think hard. Internet accounts? Same story. 40%? Great. You're in software? What's your computer? When did you buy it? 2 years ago? Did you deduct it then? Nope? OK, so we're going to depreciate it, that will be another $600 or so of which we'll allocate $400 to the business and $200 to you personally.
I thought I was pretty good at this. My accountants are much better. We both color within the lines; they were just aware of entire other coloring books that nobody had told me about. (Most recent example: the Japanese government is sending me a wire for $600 because this year, instead of filing as exempt from paying sales taxes because all the products I make are exported, I am filing a return which shows me paying $0 in sales taxes on all $0 of my Japan-source sales. What on earth is the difference? Well, if you're an exempt business, you can't claim back sales taxes you paid against sales taxes you owe the government. If you're not an exempt business, you can. If you paid more in sales taxes than your tax liability, the government wires you the difference.)
It would be like a non-tech person saying they don't need any fancy expensive software like a database because you're just paying for over-complicated solution. Then that person goes and builds out a massive Excel file with thousands of records across multiple sheets and vlookups.
