Tax software alternatives to TurboTax and H&R Block? Need recommendations for W-2 and 1099 filing

Does FreeTaxUSA handle rental income too? I have W-2s and a 1099 like OP but also have a rental property. And how long did it take you to complete everything? TurboTax took me like 4 hours last year which was ridiculous.

Yes, FreeTaxUSA absolutely handles rental income with a dedicated section for it. They guide you through all the rental-related deductions like mortgage interest, property taxes, depreciation, and maintenance expenses. I usually complete my return in about 90 minutes total, even with multiple income sources. The interface is more streamlined than TurboTax - less animations and marketing stuff slowing things down. They save your info from previous years too, which speeds things up even more if you're a returning customer.

Does it handle more complicated situations? I have W-2s and 1099s but also some investment income and a side business. Would taxr.ai work for me or is it mainly for simpler returns?

How secure is it though? I'm always nervous about uploading my tax documents to new services. Do they have good encryption and privacy practices? That's my biggest concern with trying new tax platforms.

It absolutely handles more complex situations including investment income and side businesses. The system is designed to work with all tax scenarios, from simple to complex. It has dedicated sections for investment income that guide you through capital gains, dividends, and other investment-related items. For side businesses, it offers comprehensive expense tracking and deduction suggestions based on your industry. Security is a top priority for them. They use bank-level encryption for all document uploads and data storage. All information is encrypted both in transit and at rest, and they have a strict privacy policy that prohibits selling your data. They're also SOC 2 compliant, which is an important security certification for handling financial information. I was hesitant at first too, but their security credentials are actually better than some of the bigger names.

Wait, how does that even work? The IRS phone lines are always jammed. Are you saying this service somehow gets you through the phone queue faster? I don't understand how that's possible.

Sounds like BS honestly. I've tried everything to get through to the IRS and nothing works. How could some random service magically get you to the front of the line? They probably just keep you on hold the same amount of time and charge you for it.

It works by using an algorithm that navigates the IRS phone system and holds your place in line. When an agent is about to answer, you get a call connecting you directly. It's not magic - it's smart technology that deals with the hold time so you don't have to. I was skeptical too before trying it. But the difference is they have automated systems doing the waiting instead of you sitting on the phone for hours. I spent 6+ hours over 3 days trying to get through before using Claimyr. With their service, I got connected in about 12 minutes. The IRS agent I spoke with answered all my questions about reporting my 1099 income properly, which no software could clearly explain.

Does CashApp Taxes handle cryptocurrency transactions? I did a bit of trading last year along with my regular job and some freelance work, so I need something that can deal with all of that.

CashApp Taxes has basic support for cryptocurrency transactions, but it's somewhat limited. You'll need to enter your transactions manually or import a summary from your exchange. For more complex crypto situations with lots of trades, you might want a more specialized solution. For your combination of W-2, freelance, and crypto income, TaxAct might actually be the better choice. Their crypto reporting tools are more robust and they integrate with several popular crypto exchanges for easier importing. They've really improved their crypto support over the last couple years as it's become more common.

Have you ever had your return audited using OLT? I'm always worried the cheap options might miss something or not be as thorough.

Just checked out OLT - that price is insane! But their website looks super dated. Does it handle Schedule C for self-employed people well? And how's the user experience? I don't mind basic interface if it works properly.