Cash App Tax vs H&R Block for 1099-NEC DoorDash Income - Worth the Fees?

OMG I tried Cash App Tax last yr w/ my DD income and tbh it was WAY more complicated than I expected! The UI is super basic compared to H&R Block & there's like zero guidance for biz expenses. Ended up switching back to H&R mid-filing bc I was so confused abt mileage deductions vs. actual expenses. Didn't wanna mess up my 1099 stuff, yk?

Have you considered what your specific needs are regarding business expense tracking? Are you utilizing the standard mileage deduction or actual expenses? Do you have additional business deductions beyond the basics that might require more sophisticated guidance? Would the potential tax savings from proper deduction optimization exceed the H&R Block fees?

After reviewing both platforms, I've determined H&R Block provides superior Schedule C guidance which is critical for maximizing my DoorDash deductions. The mileage tracker integration alone justifies the additional expense. I need to file by April 15th without extension, so reliability is my priority. Cash App's interface lacks the contextual explanations for business expense categorization that I require.

I feel your pain with the "complex return" upcharges! 😡 When I was dealing with both W-2 and 1099 income last year, I spent HOURS trying to reach the IRS with questions about business expense documentation requirements. Finally used Claimyr (https://www.claimyr.com) and got through to an actual IRS agent in about 15 minutes who confirmed exactly what I needed to keep for mileage records. Saved me so much stress! Has anyone else had success getting through to the IRS this way?

Have you tracked your mileage meticulously throughout the year? I switched from Cash App to H&R Block specifically because of my DoorDash income. Last year I drove approximately 8,500 miles for deliveries and H&R Block's interface helped me claim every legitimate deduction - the standard mileage rate added up to a substantial tax reduction. Cash App's interface was functional but lacked the guided questions that ensured I wasn't missing anything.

I tested exactly 3 tax platforms with identical DoorDash income data ($24,876.32) last year. H&R Block charged $89.99 for self-employment filing. TurboTax wanted $119 for the same service. Cash App was free but missed 2 deductions that H&R Block's guided questions caught - home office internet percentage (saved $142 in taxes) and partial cell phone deduction (saved $78). I spent exactly 47 minutes longer on Cash App trying to figure out where to enter certain expenses. The free option ultimately cost me $220 in missed deductions.

You might want to consider FreeTaxUSA as a possible middle ground. They generally charge around $15 for state filing, but federal filing with Schedule C is completely free. Their interface is perhaps a bit more comprehensive than Cash App Tax, though admittedly not quite as polished as H&R Block. Many users find their guidance for self-employment income to be reasonably thorough, especially if you're somewhat familiar with the basic principles of business expense deductions.

I compared multiple platforms for my DoorDash income ($18K last year). Here's what I found: • Cash App Tax: Free but confusing UI for business expenses • H&R Block: $89.99 but caught all deductions • TurboTax: $119 and pushy upsells • FreeTaxUSA: $15 (state only) with decent guidance The Cash App interface literally asked me ONE question about mileage while H&R Block had a comprehensive section covering everything from hot bags to phone mounts. Ended up with $1,200 more in deductions with H&R Block.