12 With your income difference ($95,000 vs. $42,000), you'd likely receive a "marriage bonus" by filing jointly. The marriage penalty typically affects couples when both spouses earn high, similar incomes that push them into higher tax brackets when combined. In your case, your higher income would be partially taxed at your fiancée's lower rates when combined, resulting in tax savings. Based on 2025 projected tax brackets, you could save approximately $2,100-$2,800 by filing jointly compared to both filing as single. The exact amount depends on your deductions, credits, and other tax situations, but with that income spread, you're definitely in the "bonus" category rather than the "penalty" zone.

10 When you updated your W-4s, did you have to do anything special? Or just check the "married" box? I'm getting married in June and don't want to mess this up.

9 Just checking the "married" box isn't enough! The W-4 form changed a few years ago, and you actually need to coordinate between both spouses now. If both of you work, there's a specific section for "multiple jobs" that you need to complete. The easiest way is to use the IRS withholding calculator online. My husband and I both had to adjust our withholding amounts to account for our combined income pushing us into a higher bracket. One of us actually had to withhold at the "single" rate even though we're married to avoid owing at tax time. It's confusing but worth getting right!

Whoa I had no idea there were different penalties! So if I file on time but can't pay everything, I'll only get the smaller penalty? Is there any way to avoid penalties completely if I just need like an extra month to pay?

Exactly! Always file on time even if you can't pay - the filing penalty is 10 times higher than the payment penalty. It's one of the most expensive mistakes new filers make. If you just need an extra month or two, you might qualify for a short-term payment plan with minimal or no setup fee through the IRS website. For extremely short delays (like a few weeks), sometimes you can call and request a one-time extension without penalties, but this is case-by-case and not guaranteed. Your best bet is to pay as much as you can by April 15th to minimize the amount subject to penalties, then set up a formal payment arrangement for the rest.

Most states align their deadlines with the federal April 15 date, but not all do! For example, Virginia's deadline is May 1st, and Hawaii's is April 20th. Always check your specific state's tax website to confirm.

1 I've heard about the S-Corp option but wasn't sure if it was worth the extra paperwork and compliance requirements. What income level do you think makes the S-Corp election worthwhile? And did you need to hire a specialized accountant to handle it?

22 Most tax professionals suggest considering S-Corp election when your business profit exceeds about $40,000-$50,000 annually. That's typically where the self-employment tax savings outweigh the additional costs of compliance. I did hire a specialized accountant because the S-Corp has more filing requirements including an annual 1120S corporate return. The costs run me about $1,200 annually for tax preparation, but I save around $4,000 in self-employment taxes, so it's definitely worth it. You'll also need to run regular payroll and maintain more formal business documentation, but the tax savings can be significant once your business is consistently profitable.

11 I used TurboTax Self-Employed last year for my single-member LLC with both 1099s and W-2 (I pay myself). It worked well and walked me through reporting the 1099 income on Schedule C, entering business expenses (including my salary to myself), and then separately entering my W-2. Just make sure you enter your salary as a wage expense on Schedule C - this is critical to avoid double taxation.

Do those services automatically generate and file the 1099-NECs at the end of the year? That's my biggest headache with contractors.

Yes, all three services I mentioned can automatically generate and e-file 1099-NECs based on the payments you've processed through them throughout the year. They collect and verify contractor W-9 information upfront and track all payments. QuickBooks is probably the most comprehensive if you use their accounting system too, but even standalone Melio or Bill.com will handle the 1099 filing process. They usually charge a small fee per 1099 (like $3-5 each), but the time saved and accuracy is absolutely worth it compared to manually preparing them.

I agree with this. I've been running a small photography business for 5 years and have occasionally messed up payment classifications. As long as you issue the correct 1099s at tax time, how you actually transferred the money is less important. The IRS wants the income reported correctly on both sides.

Thanks for the suggestion! I've actually been thinking about getting out of real estate altogether, so a 1031 exchange probably isn't right for me at this point. But I appreciate the idea - if I was looking to stay in the landlord business, that would definitely be something to consider to avoid the recapture hit.

Yes, an installment sale can help spread out the tax hit. When you sell with owner financing and receive payments over multiple years, you can spread the depreciation recapture tax over the payment period rather than paying it all in year one. However, there's a catch - if the mortgage on your property exceeds your basis, you might face something called "mortgage over basis" that can trigger immediate gain recognition.