That price seems high but not crazy depending on where you live. I'm in NYC and was quoted $3200 for a similar situation (W-2 plus freelance plus a rental condo). I ended up using H&R Block Premium and it handled everything fine. Just make sure to keep REALLY good records of your rental expenses and freelance costs. The software walks you through everything. The biggest issue with rental property is properly calculating depreciation and understanding what expenses can be deducted vs capitalized. If you research those topics specifically, the rest is pretty straightforward in most software packages.

That quote does seem excessive! I'm a tax preparer myself, and while rental property plus freelance income does add complexity, $2700 is on the very high end unless you have some unusual circumstances they didn't mention. Here's what I'd suggest: Get at least 2-3 more quotes from different types of tax professionals - CPAs, enrolled agents, and even some of the larger chains like H&R Block. Prices can vary wildly even for the same work. That said, given your comfort level with TurboTax in the past, you might be surprised how well the premium versions handle rental properties now. TurboTax Premier or H&R Block Premium can walk you through Schedule E for rental income and Schedule C for freelance work. The key is having organized records and taking your time. One middle-ground option: prepare your return using software first, then pay a CPA just to review it before filing. This usually costs $200-400 but gives you professional oversight without the full preparation fee. Many CPAs offer this service and it might give you peace of mind for your first year with the rental property.

Has anyone used the TurboTax iPad app for filing with rental property income? Im worried it might be too basic for handling depreciation schedules and expense tracking compared to the desktop version.

I'm in a similar boat - had to sell our desktop computer last year and only have iPhones and an iPad now. From what everyone's saying here, it sounds like there are actually several good mobile options for filing taxes with more complex situations like ours. The TurboTax mobile app seems like the safest bet since you're already familiar with their interface and trust their results. I appreciate @Oliver Cheng explaining that it has all the same features as the desktop version - that's exactly what I was worried about missing. @Taylor To's recommendation of taxr.ai sounds intriguing too, especially the document scanning feature. That would save so much time compared to manually entering all those numbers from W-2s and 1099s. Though I'm curious about the cost comparison between that and TurboTax Deluxe. Ashley, given your specific needs with mortgage deductions, charitable donations, and education credits, I'd probably start with the TurboTax app since you know it works well for your situation. You can always download it and explore the interface before committing to purchase the Deluxe upgrade. The fact that you can switch between your iPhone and iPad seamlessly is a huge plus too. The filing deadline stress is real - but it sounds like you have some solid mobile options to choose from!

I've been at the IRS for 7 years in the Small Business division. If u want advancement potential, look into the Commissioner's Office management track. Those positions can rise to GS-15 fairly quickly. But personally, I think the "best" jobs are the ones with work/life balance and decent pay without crazy stress. Appeals Officers have it pretty good imo. They're usually GS-13/14, work independently reviewing cases, and have lots of flexibility. They don't have the insane caseloads that revenue agents juggle. But you usually need to put in time as a revenue agent first to understand the processes. One overlooked option: the Taxpayer Advocate Service. They help resolve taxpayer problems and recommend systemic changes. Great mission if u care about improving the system instead of just enforcing it.

I'm currently an enrolled agent who previously worked for the IRS. If you have accounting/finance background but don't wanna do the typical revenue agent stuff, consider the National Research Program. Analyzes random tax returns to understand compliance issues. Super interesting if you like data and research. Also, working at IRS gives amazing job security and benefits compared to public accounting! The hours are actually reasonable and there's no "busy season" that consumes your life. Nobody gets rich at the IRS, but the pension + TSP (govt 401k) + healthcare is hard to beat for long-term stability.

Have you looked into making an S-corp election? I deliver for UberEats full time and switched to an S-corp structure last year. Saved me about $4500 in self-employment taxes. Basically you form an LLC, elect S-corp tax treatment, pay yourself a reasonable salary (which still gets regular employment taxes), but then you can take the rest as distributions which AREN'T subject to self-employment tax. There are some costs involved with setup and you need to run payroll, but if you're making $40k+ it's often worth it.

Hey Sophia! I totally get the panic - I was in your exact shoes two years ago making around $38k with delivery apps. The good news is it's not as scary as it seems once you understand the basics. Here's the real deal: You won't owe 30-40% to the IRS. That person was probably mixing up gross vs net income. As a gig worker, you'll pay self-employment tax (about 15.3%) plus regular income tax on your profits AFTER deductions. With proper deductions (especially mileage), your effective tax rate will likely be closer to 15-20%. Your mileage tracking in a notebook is perfect! That's going to be your biggest deduction. Also track things like: - Phone bill (business portion) - Insulated delivery bags - Car washes if you clean your car for work - Any other delivery-related expenses For the quarterly payments - yes, you should have been making them, but don't panic. The penalty isn't huge for first-time situations, especially if you file and pay on time. Going forward, set aside about 25% of your earnings each week for taxes. One last tip: consider getting help this year since it's your first time. Whether that's a tax pro, software designed for gig workers, or even calling the IRS directly for guidance. It's worth the investment to get it right and understand the process for next year. You've got this! The tax stuff seems overwhelming at first but becomes routine once you learn the system.

This is incredibly valuable information - thank you for sharing your insider perspective! I've been getting those tax relief ads constantly and was actually considering calling one of them. The fact that they charge based on income rather than actual work performed is particularly shocking. One thing I'm curious about - you mentioned that very few people actually qualify for an Offer in Compromise. What are the typical requirements for someone to be eligible? I've heard the ads claim they can get people "pennies on the dollar" settlements, but it sounds like that's mostly false advertising. Also, for someone who wants to pursue these options themselves, are there any specific IRS forms or resources you'd recommend starting with? It would be helpful to know the exact steps to take rather than getting trapped by these predatory companies.

This is an incredibly eye-opening post that everyone dealing with tax issues needs to read. The breakdown of how these companies operate - especially the "investigation phase" that's literally just ordering transcripts you can get for free - is shocking but not surprising. I'm particularly disturbed by the targeting of vulnerable populations you mentioned. It's predatory to specifically go after elderly people, veterans, and those already struggling financially. These are exactly the people who can least afford to waste thousands on services they could handle themselves. One thing I'd add for anyone reading this: if you're scared of dealing with the IRS directly, remember that ignoring the problem or paying these inflated fees to middlemen only makes things worse. The IRS actually has taxpayer advocates and offers free resources through VITA programs for lower-income taxpayers. Has anyone here successfully handled their own tax resolution after initially considering one of these companies? It would be helpful to hear some success stories to encourage others to take the DIY approach rather than getting scammed.