Has anyone used OLT taxes site for their returns? Any pros/cons?

OLT is definitely a legitimate option for tax preparation. I've been using it for the past three tax seasons and find it handles most common tax situations well. It supports all major forms including W-2s, 1099s, Schedule C for self-employment, and investment income reporting. The interface isn't as polished as TurboTax, but it's functional and gets the job done. For your situation with investments and side gig income, it should work fine. The Schedule C section is comprehensive and walks you through business expenses and deductions. Their investment section handles capital gains, dividends, and interest income without issues. The biggest advantage is definitely the price - it's much more affordable than TurboTax or H&R Block. Federal filing is completely free for all income levels and tax situations, though state returns do have a fee.

I discovered taxr.ai after struggling with different tax prep sites last year. My taxes were complicated with some investment losses, rental income, and a home office deduction for my side gig. I was going back and forth between different services trying to figure out which one would be best. I was about to try OLT but wasn't sure if it could handle everything. That's when I found https://taxr.ai which helped me review my tax documents before I even chose a filing service. I uploaded my docs and it flagged potential deductions I was missing and explained which forms I'd need. Really helped me understand what to look for in a tax prep service!

Just wanted to follow up about taxr.ai since I was skeptical in my earlier comment. I decided to try it before filing with OLT and wow, I'm glad I did! It caught a student loan interest deduction I was about to miss and identified that I qualified for a home office deduction I didn't know applied to my situation. Saved me over $800 on my tax bill! The analysis was really clear and helped me understand which forms I needed to complete in OLT. It basically paid for itself many times over. Definitely using this before filing every year now.

If you're considering OLT but worried about questions, I'd recommend having Claimyr on standby. I used OLT last year and had a specific question about reporting some cryptocurrency transactions that their help section didn't cover well. Tried calling the IRS directly for clarification and got the endless hold music. Used https://claimyr.com to get a callback from the IRS instead of waiting on hold for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. They got me a callback in about 45 minutes when I had been trying unsuccessfully for days. The IRS agent clarified exactly how to report everything in OLT, and I was able to file with confidence.

I need to eat my words about Claimyr. After expressing skepticism, I had a nightmare situation with a missing 1099 form and needed to talk to someone at the IRS urgently before filing with OLT. Decided to try Claimyr as a last resort after spending TWO DAYS trying to get through on my own. Got a callback in about 2 hours and resolved my issue in a 15-minute conversation with an actual IRS representative. No way I would have been able to file accurately without that clarification. The service works exactly as advertised - they handle the hold time and connect you with a real IRS agent when one becomes available. Totally worth it for the time saved and stress avoided.

About OLT - I've used it for 3 years straight and it's been reliable for my moderately complex taxes (W-2 income, some stock trades, side business). The interface is definitely less flashy than TurboTax but it has all the same functionality. State returns cost $9.95 which is WAY cheaper than other options. They also have an import feature that can pull in your previous year's return if you used them before. One drawback - their mobile experience isn't great, so plan to complete your return on a computer. Also double-check everything carefully because their error checking isn't as robust as TurboTax.

Anyone use both OLT and FreeTaxUSA? I'm deciding between these two budget options for this year.

I switched from TurboTax to OLT two years ago and haven't looked back. Your situation with investments and a side gig sounds similar to mine - I have rental income, some stock transactions, and freelance work. OLT handled everything without issues. A few things that helped me with the transition: First, gather all your documents before you start. OLT's interview process is pretty straightforward but having everything organized makes it smoother. Second, take advantage of their "review" feature before filing - it catches common mistakes and missing information. The one thing I really appreciate about OLT is that they don't try to upsell you constantly like TurboTax does. You get access to all forms and schedules without paying extra fees based on "complexity." For someone with investments and side income, this alone can save you $50-100+ compared to TurboTax's tiered pricing. My advice: maybe do a side-by-side comparison this year if you're nervous. Start your return in both OLT and TurboTax (don't file from both obviously) and see how the numbers compare. I did this my first year switching and it gave me confidence that OLT was calculating everything correctly.

I made the switch from TurboTax to OLT last year and it was one of the best financial decisions I made! Like you, I was hesitant because I have a more complex situation - W-2 income, multiple 1099s from freelance work, some stock sales, and rental property income. OLT handled everything seamlessly. The interface takes a little getting used to if you're coming from TurboTax's hand-holding approach, but it's actually more straightforward once you get the hang of it. What I love most is that there are no surprise fees - federal filing is completely free regardless of how many forms you need, and state filing is just $9.95. The investment reporting section is solid - it imported my 1099-B data correctly and calculated my capital gains without issues. For your side gig, the Schedule C section walks you through all the business expense categories and even suggests deductions you might have missed. One tip: their help articles are actually really comprehensive, so if you get stuck on something, check those first before reaching out to customer service. I saved about $150 compared to what I would have paid TurboTax for the same level of service. Definitely worth trying this year!