Ok this might sound dumb but I had a similar issue and realized I was looking at an outdated form. Double check you have the 2024 version of Form 8959? They made some changes to the Additional Medicare Tax calculation in recent years. Also check if ur tax software is up to date. TurboTax automatically updated for me mid-filing season last year cuz there was some correction to one of the forms.

I've been dealing with Form 8959 for several years now and you're not going crazy - there have definitely been some confusing aspects to the Additional Medicare Tax calculations. The most common issue I see is with Line 22 when people have income right around the threshold amounts. One thing that might help: make sure you're using the most current version of both the form and instructions. The IRS has made several revisions over the years, and sometimes the earlier versions had calculation errors or unclear guidance. For your situation with $275k income as a single filer, you should be calculating Additional Medicare Tax on the amount over $200k. If the worksheet is giving you a different result than what seems logical, try working backwards from the tax code itself - Section 1411 of the IRC is pretty clear about the 0.9% rate on income exceeding the threshold. Document your calculation method thoroughly regardless of which approach you take. If there really is an error in the form instructions, having clear documentation of your reasoning will protect you later.

Unlike a missed 1099 or unreported income, which can trigger serious penalties, a health insurance gap is much less concerning these days. I've prepared hundreds of returns with coverage gaps since 2019, and none have faced federal penalties. It's nothing like the 2014-2018 period when penalties could run into thousands of dollars. Still, document everything carefully - if you're in California or Massachusetts, the state implications are real and can be substantial compared to other tax adjustments.

Just to add some reassurance from someone who went through this exact situation - I had a 3-month gap in 2022 when I transitioned between jobs, very similar to your October-January timeline. I was also worried about doing something wrong on my taxes since I'd been self-preparing for years. The reality was much simpler than I expected. I accurately reported that I didn't have full-year coverage, indicated the months I was covered vs. uncovered, and that was it. No federal penalty, no impact on my refund, and no additional complications. The IRS systems are set up to handle these employment transition gaps routinely now. The key is just being honest and accurate in your reporting - don't overthink it. Your situation is incredibly common with job changes, and the tax system accounts for it. Focus your energy on the other parts of your return that might actually affect your refund amount.

Another expense to consider - property taxes during the renovation period. Unlike loan interest and utilities which can potentially be capitalized, property taxes are generally deductible on Schedule A (if you itemize) rather than being added to basis. This is true even during the renovation period. Also, make sure you're separating any personal use from the renovation timeline. If you stayed in the property at any point during renovations, you'll need to allocate expenses accordingly. The IRS is pretty strict about this - only expenses incurred while the property was held purely for investment/sale purposes can be capitalized. One last tip: keep photos documenting the before/during/after condition of the property. This helps support your position that certain expenses were truly improvements rather than just repairs or maintenance.

One thing that hasn't been mentioned yet - if you had to get any permits for your renovation work, those permit fees can definitely be added to your basis as they're directly related to the improvements. Same goes for any required inspections. Also, be careful about mixing renovation expenses with regular maintenance. For example, if you had to replace a broken window during renovation, that's maintenance/repair. But if you upgraded all the windows to energy-efficient ones as part of improving the property, those are capital improvements that increase your basis. The key test is whether the expense restores the property to its original condition (repair/maintenance) or makes it better than it was (improvement). For a flip, you're generally trying to improve the property beyond its original state, so most of your major expenses should qualify for basis treatment. Keep all your receipts organized by category - it'll make everything much easier come tax time!

Question - does anyone know if the standard deduction covers this kind of income? Like if I made $175 from surveys but take the standard deduction of $13,850 (for 2024), do I still need to file a Schedule C? Seems like overkill for such a small amount.

I've been doing survey work for about two years now and want to share what I've learned about the tax side. Even small amounts need to be reported - I learned this the hard way when I skipped reporting $89 one year and got a letter from the IRS later (apparently one of the survey companies did report it even though they didn't send me a 1099). For amounts under $400, you don't owe self-employment tax, but you still report the income on Schedule C. I list my business as "Online Market Research" and it's pretty straightforward. The key is keeping good records throughout the year - I use a simple spreadsheet with the date, platform name, and amount earned. One tip: if you use your phone or computer primarily for surveys, you can deduct a percentage of those costs. I calculated that about 15% of my phone usage was for survey work and deducted that portion of my monthly bill. Just make sure you can justify the percentage if asked. The paperwork might seem excessive for small amounts, but it's better to be compliant from the start than deal with IRS questions later!

Have you considered requesting your transcript by mail instead? What about calling the practitioner priority line if you work with a tax professional? Could your tax software provider offer transcript access through their professional portal? If you need it urgently, try the automated phone system at 800-908-9946. It's ancient technology but sometimes works better than the website. Press 2 for transcripts, then follow the prompts. Takes about 5-10 days to arrive by mail, but at least you'll have it.

I've been dealing with this exact same issue! As someone who needs quarterly transcripts for my small business, I've found a few workarounds that might help: **What's worked for me:** - The mobile app (IRS2Go) sometimes loads when the website won't - try that first - Incognito/private browsing mode occasionally bypasses whatever's causing the error - If you're getting the "identity verification" error, make sure your ID.me account is fully set up and linked **Backup options:** - The automated phone line (800-908-9946) is your friend - it's clunky but reliable - Request by mail using Form 4506-T if you can wait 5-10 business days - If you work with a tax pro, they might have access through practitioner channels The timing advice others mentioned is spot-on - early morning or late evening definitely helps. I've also noticed weekends tend to be less problematic than weekdays during tax season. Hope this helps! The system is definitely overloaded right now, but you should be able to get what you need through one of these methods.