Has anyone used the IRS Tax Withholding Estimator for this kind of situation? I tried it but it got super confusing when entering multiple jobs.

I had almost the exact same thing happen to me! Been working two jobs for about 4 years, and suddenly my part-time employer started withholding federal taxes right after I changed my main job. What I figured out was that the new W-4 form has this "multiple jobs worksheet" section that's way more sensitive than the old system. Even if you don't explicitly check the multiple jobs box, certain combinations of how you fill out the form can trigger withholding changes across employers. The easiest fix is to go to your HR department at your full-time job and ask for a blank W-4. Fill it out exactly like your old one (conservative approach - just your basic info and filing status, no extra complications). That should reset things back to how they were. You can also submit a new W-4 to your part-time job requesting exemption from federal withholding if you prefer to handle it all through your main job like before. I'd recommend running the numbers through a tax calculator first though to make sure you're still withholding enough overall - the new system might actually be more accurate for your situation even if it's annoying!

I've been using AI tax tools for the past two years and I'm honestly impressed with how much they've improved. The key is choosing a reputable one and understanding its limitations. For your situation - W-2, some 1099 income, and mortgage interest - most good AI tax services should handle this just fine. The mortgage interest deduction is pretty straightforward, and the 1099 reporting isn't too complex at that income level. What I really like about AI tax tools is they often catch deductions I wouldn't have thought of. Last year mine suggested a home office deduction for my freelance work that saved me hundreds. They also explain everything in plain English instead of tax jargon. That said, I'd recommend doing a bit of research before choosing one. Read reviews, check their security practices, and make sure they offer some kind of support if you run into issues. Some people mentioned good experiences with specific services in this thread that might be worth looking into. The biggest advantage for me has been the cost savings - I was paying my accountant $400+ every year and now I spend maybe $50-75 on the AI service with better results.

I've been working in tax preparation for over 15 years, and I have to say the AI tools have gotten surprisingly sophisticated. For someone with your tax situation - W-2, moderate 1099 income, and first-time homeowner deductions - AI should handle it well. The mortgage interest deduction is one of the most straightforward deductions to process, and $14k in 1099 income puts you in a sweet spot where the calculations aren't overly complex but there are still potential business deductions to explore. One thing I'd suggest is making sure whatever AI service you choose can properly handle quarterly estimated tax calculations for next year. With that level of 1099 income, you'll likely need to make estimated payments in 2025 to avoid underpayment penalties. A good AI tool should automatically calculate these and remind you when they're due. Also, don't overlook potential deductions related to your side gig - things like business use of your phone, internet, equipment, supplies, or even a portion of your home if you use it exclusively for work. AI tools are getting much better at identifying these opportunities through targeted questions. The audit protection offered by most reputable AI services is comparable to what you'd get from TurboTax, so that shouldn't be a major concern. Just make sure to keep all your supporting documents regardless of which method you choose.

One thing nobody's mentioned - you might want to get a professional appraisal retroactive to the date of death. This establishes the stepped-up basis and gives you solid documentation if the IRS ever questions the values. They usually cost around $400-500 but can save thousands in potential taxes or penalties.

I'm so sorry for your loss, and I completely understand feeling overwhelmed - handling a deceased person's taxes is incredibly stressful, especially when you're doing it as a volunteer. Since you found last year's depreciation schedule, that's actually your golden ticket! Look for these key numbers on that document: the original cost basis (what she paid in 1989), accumulated depreciation through last year, and the annual depreciation amount. These should all be listed on Schedule E or Form 4562 from her prior return. For the missing pieces like land value, you can often use a rule of thumb that land typically represents 20-30% of the total purchase price for residential properties, though this varies by location. The county assessor's office can also provide the land-to-improvement ratio they use for tax purposes. One important thing - since this is a final return for someone who passed away, you'll need to calculate depreciation only up to the date of death, not for the full year. After death, the property gets a stepped-up basis to fair market value, which eliminates future depreciation but may trigger depreciation recapture that needs to be reported on the final return. Don't hesitate to call the IRS taxpayer assistance line if you get stuck - they're usually helpful with estate-related questions, though you may need patience with hold times. You're doing a wonderful thing helping with her final affairs.

Just wanted to share my experience filing Form 1120-F from the UK last year. I was initially overwhelmed by all the requirements, but here's what worked for me: 1. **Documentation is key** - Beyond the forms themselves, I included a detailed reconciliation statement showing how my UK financial statements tied to the US tax return. This seemed to help with processing. 2. **Treaty position disclosure** - For Form 8833, be very specific about which treaty articles you're relying on. I initially filed a vague disclosure and got a follow-up letter asking for clarification, which delayed everything by months. 3. **Banking considerations** - If you need to make any tax payments, set up your international wire transfer well in advance. My UK bank required additional documentation for US tax payments that took weeks to process. 4. **Keep multiple copies** - I kept photocopies of everything I mailed, plus digital scans. When I had questions later, having exact copies of what I filed was invaluable. The whole process took about 6 weeks from mailing to receiving confirmation of processing. Definitely start early and don't underestimate the time needed for international mail delivery!

I've been filing Form 1120-F from Germany for the past three years and wanted to share a few additional tips that might help: **Timeline planning**: Start the process at least 8-10 weeks before the deadline. International mail can be unpredictable, and if there are any issues with your filing, you'll need time to respond. I learned this the hard way when my first filing got delayed due to missing signatures. **Currency conversion**: Make sure you're using consistent exchange rates throughout your forms. The IRS generally accepts year-end rates or average rates for the tax year, but you need to be consistent and document which method you used. I include a brief statement with my filing explaining my currency conversion methodology. **State filing considerations**: Don't forget to check if you need to file state returns as well. If your foreign corporation has effectively connected income, you might need to file in multiple states depending on where that income is sourced. **Professional help**: While the DIY approach can work, I'd strongly recommend at least having a US tax professional review your first filing. The penalties for errors on international corporate returns can be substantial, and the complexity is much higher than domestic filings. The learning curve is steep, but it gets easier after the first year once you understand the process!

Has anyone used one of those insurance comparison sites for commercial auto policies? I found the prices vary WILDLY between companies when I was shopping for my food truck.

Just went through this exact situation with my consulting business last month! After reading all the advice here, I ended up getting a commercial auto policy for my business vehicle and I'm so glad I did. The peace of mind is worth it alone. One thing I learned that might help - some insurance companies offer "artisan" or "contractor" policies specifically designed for businesses like photography that use vehicles to transport equipment to job sites. These policies often include coverage for the equipment itself while it's being transported, which could be valuable for your wife's photography gear. I'd definitely recommend getting quotes from both your current insurance company (to see if they offer commercial policies) and some competitors. The price difference between companies was surprising - I found quotes ranging from $1,200 to $2,800 annually for basically the same coverage. Also ask about any business discounts they might offer, especially if she's getting other business insurance through the same company. The tax benefits mentioned earlier are real too. Being able to deduct 100% of the insurance premiums as a business expense makes the higher cost more manageable. Good luck with whatever you decide!