The Best Tax & Accounting Software Programs

April 16, 2019by wpx_alleviatetax0
In our digital age, it’s interesting to go back and look at the origins of what society needs prompting certain technological advances, like the way we are fascinated by museum artifacts and antiques that give us a glimpse of what life was like in another era.

The history of accounting can be traced back to ancient civilizations and is closely related to developments in writing, counting, money, and early auditing systems by the Egyptians, Mesopotamians, Greeks, and Babylonians. IN 1000 B.C., the Phoenicians created an alphabet with accounting so that they were not cheated through trades with ancient Egyptians. Accountancy migrated to Europe towards the end of the Crusades, which saw a rise in trade between Europe and the Middle East. During the Industrial Revolution, the auditing profession was created to verify what was going into and coming out of storehouses.

In the 1490’s, Luca Pacioli, the father of accounting, wrote a famous white paper called “Everything about Arithmetic, Geometry, and Proportion.” The treatise is based on research that he performed on the common practices of merchants in Venice, Milan, and Florence. He revealed that several merchants kept books of debts “he owes” as well as credits which means “he trusts.”

Before computers, bookkeepers relied on paper ledgers to record debits and credits, revenue and expenses. Gone are the days of hand-written financial records and mailing in tax returns which we painstakingly wrote on with our most legible penmanship. Machines such as calculators began to play a technological role in the 1800s, by the end of the century the punch-card machine was invented to speed up data, and the invention of computers completely transformed accounting in the 20th century.

When the IRS first began using computers in 1961, people were horrified. A controversy surrounding the IRS computers was reflected in the mass media. “Right on the Button” is an entertaining short film that the IRS made in the 1960’s to highlight the benefits of a computerized system and alleviate people’s fears of “Big Brother” taking over. To quell fears that computers would replace human jobs, the film emphasizes the IRS employees who are vital in maintaining and checking the system.


Video Credit: US National Archives

The shift towards computerized tax processing was revolutionary in speeding up processing times, discovering the errors that taxpayers made, catching tax evaders and scammers, and verifying that all U.S. citizens were paying a fair amount each year.

The Accounting Journal describes early accounting software as “handcrafted byte by byte over the course of months.” As computers became powerful, programmers created more platforms that could serve many different customers.

In the mid 80’s personal computers came out and soon there were several companies selling accounting software. The early versions were expensive and customizable, but as the market became more competitive, prices dropped drastically, and software was standardized to accommodate customer service needs. Peach Tree and Quick Books quickly dominated because they were the more reliable than small, independent software developers.

In the early 1990’s, a game-changing operating system called Linux was released to the public. It was an unprecedented jolt to the software industry, revolutionizing open source software and pioneering the path to web-based software.

Today, accounting software has advanced to such a degree that it’s able to handle every detail of money tracking, whether that means day-to-day bookkeeping for small businesses and independent contractors, or those seeking a more efficient way to do their taxes.

Tax software packages come in cloud-based and/or desktop versions. Cloud versions are convenient because the software and your return are housed online, which means you can access them through all of your devices with the same login credentials.

Nowadays, we can’t even imagine having to go through tedious manual processes to manage our finances. The challenge is how to choose the right tax and accounting software when there are so many options. Here’s a roundup of the best the market has to offer.


TurboTax stands out for its design and a workflow that makes it easy to enter all your tax information. It’s user-friendly, interview-style Q&A is like having a chat with a tax preparer who asks useful questions and knows where to put the answers on your return.

Paid users can get free, real-time help from a tax specialist through video using the TurboTax mobile app, and there’s an extensive resource for answers and research. A new feature is TurboTax Live—a high-end package that can handle virtually every form the IRS may throw at you, plus you get a one-on-one review with an actual Enrolled Agent or CPA before you file, as well as unlimited live tax advice from an on-screen CPA or EA.

TurboTax is more expensive than some of the other options. It easily costs over $100 for software and state-return preparation, depending on the version. However, if you google “TurboTax discount code” you can usually save $10-$30 every year, and the military can save up to $49. TurboTax offers free guidance if you get audited, but if you want actual representation before the IRS, you’ll need to buy the Audit Defense add-on product for $44.99.

Reportedly, Turbo Tax has some issues with integrating their accounts with their own various apps, but overall, it’s one of the most popular choices.


The Best Tax & Accounting Software Programs

H&R Block’s interface wins points for being user-friendly and offering exceptional support. Paid versions allow you to import the previous year’s return from TurboTax, Tax Act, or any other tax prep company. It includes useful tools like a W-2 and 1099 photo import, which saves time on keying in numbers.

Because the software is housed online, you can log in from other devices if you prefer to chip away at your return here and there rather than all at once. The mobile app was recently redesigned to accommodate you doing your return entirely through your phone if you wish.

The chances are that you’ll have some questions during the tax preparation process, and H&R Block offers several robust support options. Many accounting terms are hyperlinked to clarify how specific terminology applies to you, and the software is quick to send confused users to a searchable knowledge base. Like most software packages, a banner runs across the top of the page to keep track of where you are in the process. Deluxe and Premium package users also get free online chat with a tax professional.

H&R Block users always have the option to visit one of the thousands of brick-and-mortar offices staffed with experts who can help with your return if it becomes overwhelming, and while the cost of this isn’t included with the software, they will be able to make sense of your haphazard calculations at a reasonable rate.

H&R Block also offers Tax Pro Review, an add-on that costs anywhere from $49.99 and $89.99 depending on which software version you buy. The tax pros handling these returns are “certified at H&R Block’s highest levels and are our most tenured and experienced tax professionals,” according to the company.

For an extra $19.99, you can purchase an add-on called Worry-Free Audit Support. This gets you one-on-one contact with a tax professional to help guide you through an audit and includes IRS correspondence management, audit preparation, and in-person audit representation.


The Best Tax & Accounting Software Programs

QuickBooks is a comprehensive accounting software package developed and marketed by Intuit. Its wide range of products is geared towards small and medium-sized businesses and offer physical software accounting programs as well as cloud-based versions that manage invoices and pay bills, perform payroll functions, and organize write-offs for tax returns.

The ability to integrate with other programs is a significant advantage of QuickBooks. After using the product to input business income and expenses, users can easily export that data to their favorite tax preparation program to make filing income taxes less tedious. Receipt Capture is a feature that allows you to take photos of your receipts and link them to expenses right from your phone.

When QuickBooks’ online version was first released, users complained of sporadic crashes, random blue screens, and other anomalies, making it less than the equivalent of QuickBooks’ desktop version. Fortunately, updates have solved all the issues involving slow running speeds, the overall stability has strengthened, and the user experience is much better.

Another plus is the 24-hour support that’s included with all the QuickBooks plans. The first three months of all QuickBooks programs are currently discounted on their website, so take advantage of this offer while you can.

SAGE 50 (formerly PeachTree) 

For years, QuickBooks and Peachtree (now Sage 50) were the gold standards in small business accounting software. QuickBooks still holds 89 percent of the small business accounting software market in America, but Sage 50 is an increasingly popular product that’s giving QuickBooks a run for their money.

Sage 50 provides secure billing and invoicing, inventory and cash flow management, Enterprise-grade security, and analytics reporting. It also includes built-in data checks that flag common accounting mistakes and suspicious transactions.

You can pull your accounting data into your everyday productivity tools like Outlook and Excel. Unique features like Sage Contact and Sage Intelligence integrate directly with Microsoft Office 365. Both the Pro and Premium offerings are 40% off on Sage 50’s website for a limited time until July 21, 2018 (Promotion Code D-1929-0002), reduced from $447.78 to $267.99 and $692.58 to $414.99 per year, respectively. The difference between Pro and Premium are additional capabilities such as being able to plan and track inventory, manage jobs and expenses, and add more users.


The Best Tax & Accounting Software Programs

TaxAct is significantly less expensive than most of the competition. They offer a free version for basic returns, and the Plus version costs less than half of TurboTax’s or H&R Block’s comparable offerings. It has all the necessary features you would want, such as the ability to import last year’s returns, a W-2 import that also works with mobile devices, and some planning tools and calculators. Because the software is housed online, you can log in from other devices if you prefer to work on your return incrementally.

If you need help, TaxAct will put you in touch with a CPA or Enrolled Agent over the phone or through live chat, a rare bonus feature for software at this low price point.

TaxAct’s audit assistance consists of an FAQ page on its website, but for $39 (included in the Premium package), customers can buy a service from a partner company that includes a comprehensive response and resolution strategy, IRS and state correspondence, help with denied credits, and tax debt and tax fraud assistance.


The Best Tax & Accounting Software Programs

TaxSlayer is a steal compared to much of the competition, and its interface is as attractive as the more expensive versions on the market and has similar features such as the ability to upload images of W-2’s and 1099’s as well as an extensive online knowledge base.

TaxSlayer guarantees that unless you receive the maximum refund to which you are entitled, they will refund you the purchase price paid. Their in-depth error is checking guarantees 100% accuracy, or they will reimburse you any penalties and interest charges.

Tax help is free for Premium and Self-Employed users, along with free audit assistance (users of other versions can buy it for an additional $29.99). However, this will only help you prepare for an audit and not representation in front of the IRS, and freelancers or anyone filing a Schedule C doesn’t qualify. The support coverage applies for three years from the date you buy the software. There is no audit defense available.


The Best Tax & Accounting Software Programs

Wave is a free cloud-based accounting software geared towards small business owners and entrepreneurs, and it’s one of the best online resources for its target audience of over 2.7 million users.

It offers unlimited Invoices in any currency, Income, and Expense Tracking with the capability of receipt scanning, Payroll, and unlimited guest collaborators which means you can even give your accountant access. Wave accepts credit cards and bank payments (ACH) and allows you to run multiple business ventures through one account. You can connect Wave with PayPal, Shoeboxed, and Etsy and export financial reports in CSV or PDF format. Customizable sales taxes and at-a-glance dashboards, including cash balances and invoice status, means easy account reconciliation.


The Best Tax & Accounting Software Programs

If your income was less than $66,000 last year, you probably qualify to use the IRS’ Free File program, which gets you access to free tax-prep software. This lets you prepare and electronically file your return without a fee using software from a consortium of about a dozen tax-prep companies. Some are brand names; others are more under the radar. If you answer a few questions on the site, the IRS will match you with the right software.


If you are an independent contractor, then a CPA might be your best bet. If you have multiple sources of income, your taxes will be a lot more complicated than if you have one W-2 to record, and an accountant can help you sort through how to report everything correctly. If your income is more than $200,000 a year, an accountant is imperative since top earners are more likely to be audited.

An accountant also knows what’s new in ever-shifting tax law and can help you take advantage of the latest benefits and offer advice on what you can and cannot write-off as business expenses. An accountant can help you understand the breakdown and how to avoid future problems if you owe the IRS taxes. Most accountants understand how intimidating it can be going up against the government, and a solid CPA will stand behind you and help resolve conflicts as fast as possible.

If you’re embarking on a new business, then an accountant can help you prepare by ensuring that all necessary tax forms are filed correctly. An accountant can also assist you in improving your credit rating using tactics that speed up the process that goes beyond simply paying your bills on time.

If you inherit a significant amount of cash or property, taxes can be costly if you don’t have anyone to help you navigate the specifics. An accountant will help advise you on the present situation and help you reduce your taxes for the future. A CPA can help you negotiate with creditors and make sure you aren’t being +harassed.

If you have kids and want to contribute money to a college savings account, or even a trust, an accountant can help set all of that up. If you’re planning to leave a substantial financial gift, an accountant will have all the information on how to go about it while gaining the greatest tax benefits.

Whether you own a home or have rental properties, an accountant can help you manage the specific tax situations as well as the major benefits. Similarly, if you are about to go through a major life change, a CPA can help lead you through the transition. Anytime you get married, get divorced, retire, or have children your tax situation changes, and an accountant will help you navigate the waters.

CPA’s often also serve as consultants, offering advice regarding protection of assets, salaries, employment benefits, systems for data processing, and more. Hiring an accountant can be an excellent way to save yourself time, money, and stress. Costs will vary according to the services you request.


Moving from paper to computer was a significant evolution in accounting. Now that technology has advanced beyond the green and white alternating lines on paper that made it easier to follow a row of numbers across a 36-inch ledger page; we are entering an era when we will interface through browsers and servers rather than loading software onto our computers.

Web-based accounting packages also aid scalability. An entrepreneur can never really know if his business idea is going to attract 10,000 users or one million, so he or she must be prepared to accommodate both.

Steven Cohen, the Managing Director of Softline, recently declared, “I believe that we are seeing the final revolution in accounting software. Mobility is a new paradigm for the business world. Say all your computers were stolen. In the cloud, you’re still up and running. Now accounting packages can grow endlessly and will never be obsolete. Development takes less time. There will never again be a need to create new software because of a platform change. Web-based software can be integrated with any process anywhere in the world. There will be no more running to the accountant for various reports – it is served on demand.”

As always, the right tax and accounting software will be whatever works best for you. With all the free trials available, it’s easier than ever to test out different options before committing to buy.

Wondering which financial app would also be useful for you? Here’s a round-up of  “The 13 Best Financial Apps to Help You Manage Your Money.”

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