TurboTax or H&R Block? My Tax Software Tips & Strategies

I have a middle-of-the-road tax situation each year when tax season arrives: some complexity from being self-employed with multiple freelancing clients, but overall not one of the more complex situations that people with more assets or complicated debts might deal with.

Still, I find myself every year deciding whether to do my own taxes with tax software or to seek out a tax prep accountant to help me. I then have to decide, based on my past experiences, TurboTax or H&R Block? In the end, I almost always go with the software for a simple reason: all the time I spend gathering my materials is time I’d have to spend either way, and the software makes the rest of the process ​so easy​.

I have used TurboTax, usually their Premier or Self-Employed products, and H&R Block File Taxes Online, and both provided exactly what I needed to be able to file my taxes while feeling confident that I’ve done them correctly.

With TurboTax adding Live and H&R Block Tax Pro Go, there’s even less reason to feel compelled to find your own accountant, since a complicated tax situation can still be run by a professional if you’re worried about it.

Here are some of the reasons why I have appreciated the tax software options available to me over the past few years, and a few challenges to overcome as you consider your own tax software.

​Read More:​ Tax Preparation Software: Choose the Best Tax Software for Your Needs

TurboTax and H&R Block have had many tax cycles to perfect their usability, and it shows. Yes, taxes can be unbearably complex, but these three features were top on my list for why I enjoyed using both of these products.

Both of these software programs have really perfected the art of not overwhelming me with giant, complicated tax forms. When I look at my actual return, my eyes go a little wide, but when I’m using the software, they ask me one question at a time.

For some accounting-minded folks these software programs are probably a little cumbersome, since you have to click through some questions that don’t apply, but I think they do a pretty good job of making the experience efficient. With central pages for things like deductions or income, you can just click into the modules that apply to you and answer those questions, avoiding the sections where you, say, don’t have any income from rental properties or whatever the inapplicable section might be.

​Read More:​ The Best Tax Software for 2021 (According to Your Needs)

Both of these software programs have access to powerful technology that can either directly import your W2 or 1099 income, or will let you take a picture of the document. The photo technology can “read” the W2 and pull in the correct numbers; you just have to double-check it and move forward. Since a lot of the time I spent on software programs in the past was spent typing each item from the different boxes on the form, this is a huge time saver.

Probably my favorite aspect of tax software is that I can do a bite-sized part of it if I feel like getting something done, but the software saves my progress and I can come back to it later. The review and summary screens let me know when I’m still missing a key detail or might want to return to a given section.

Especially if a document gets delayed or changed by an employer or client, this is particularly helpful, since I can get almost everything done and wait to file once I have my last key information available.

​Read More:​ Deadlines to Submit Tax Returns

While I recommend both of these software products, I do have my cautions! Doing your taxes in the United States can present surprises even when you’re very prepared, so here are some tips to make your filing as easy as possible. Narrowing down which software product you choose could be related to whether you use QuickBooks, another Intuit product, and want easy transferability from one product to the other, or whether you're a small business owner and therefore have a preference between the way each company handles business taxes.

Both H&R Block and TurboTax by Intuit are hoping to win your business, so you may see exciting ads for a percentage off or that you can start a federal return for free. Sometimes, these are great deals, but it’s key to read the fine print. I once was in the weird situation of having to file in two different states, and I didn’t see until the end of my tax work that I would have to pay for two separate state return costs. This wasn’t the company’s fault, but digging into their plans lets you really budget for the cost of the program.

​Read More:​ When Can You Get That Tax Refund?

I am a big fan of starting my taxes much earlier than April. Since I don’t have to go ahead and file even if I start in the first week of February, starting early gives me the chance to learn if there’s some unexpected hiccup I didn’t plan for. I was waiting for information from my father’s accountant one year and didn’t hear back until mid-March, but when I got the answer, I was able to easily move forward because I hadn’t waited till the last minute to realize I needed that data.

Both of these software programs have a fun feature that gives you a live update on what your refund will be, which can be fun… when the refund amount goes up! Go into your tax process expecting that number to change a lot, since different sections of your tax software will push the number up or down.

​Read More:​ E-Filing: How to File Your Taxes Electronically, IRS Free File & More

Tax software is great, but the world of tax exceptions and exemptions is definitely wild. If you’ve been led to believe you qualify for a major tax credit or deduction but the software isn’t allowing you to get it, consider reaching out to their live support team that includes tax professionals, even CPAs. At minimum, they may suggest a slightly more expensive tier of the product, but if you get hundreds or thousands of dollars back in exchange for a $20-$50 upgrade, it’s well worth it!