Something no one mentioned yet - make sure you and your spouse don't accidentally exceed the family limit COMBINED during the transition months. When my husband and I went through this, our benefits department counted wrong and we over-contributed by accident. Had to withdraw the excess contribution before filing taxes which was a hassle because we'd already spent some of the HSA funds on medical expenses. Just double check all your calculations!

This is such a timely question! I just went through something similar when my partner switched jobs mid-year. One thing that really helped me was keeping detailed records of exactly when each coverage period started and ended - down to the specific dates, not just months. The IRS can be pretty strict about the timing, especially if there are any gaps in coverage or overlapping periods. I'd recommend documenting everything: when your wife's current coverage under your plan ends, when her new employer's coverage begins, and whether there's any continuation coverage (like COBRA) in between. Also, don't forget about the catch-up contributions if either of you is 55 or older! Those rules can get even more complex with mid-year changes. The additional $1,000 catch-up contribution follows the same monthly calculation rules, so you'd need to factor that in too. One last tip - consider setting up automatic contributions to match your calculated monthly limits rather than trying to make one large contribution at year-end. It helps avoid accidentally over-contributing and makes the whole process much more manageable.

One more thing to keep in mind - if the cabin was inherited, you likely get a "stepped-up basis" which means your cost basis is the fair market value when you inherited it, not what your grandparents originally paid. This can significantly reduce your capital gains tax! For example, if your grandparents bought the cabin for $50,000 but it was worth $200,000 when you inherited it, your basis is $200,000. If you sell it for $250,000, you only pay capital gains on the $50,000 difference, not the full $200,000 gain from the original purchase price. Make sure you have documentation of the property's value at the time of inheritance (like an appraisal from the estate) since this will be crucial for calculating your actual taxable gain. This could save you thousands in taxes compared to what you might initially think you owe!

This is exactly the situation I was in a few years ago! One thing that really helped me was understanding the "safe harbor" rule - if you pay at least 100% of last year's tax liability (or 110% if your prior year AGI was over $150,000) through withholding and estimated payments, you won't face underpayment penalties even if you end up owing more when you file. So if your total tax last year was $8,000, as long as you pay at least $8,000 this year through your regular W2 withholding plus estimated payments for the property sale, you're protected from penalties. This takes a lot of the guesswork and stress out of estimating the exact amount. I'd also recommend keeping detailed records of your property's basis (what your grandparents paid plus any improvements) since you'll need that to calculate your actual gain. Don't forget about selling expenses like realtor commissions, legal fees, and closing costs - these can be deducted from your gain and reduce your tax bill.

As someone who's dealt with similar year-end gift timing questions, I can confirm what others have said about the "unconditional delivery" rule. The IRS is actually quite reasonable about holiday banking delays - they understand that checks given in late December often can't be deposited until after New Year's due to bank closures and holiday schedules. Your situation is textbook for how gift timing works. Since you physically handed your niece the check in 2024, had sufficient funds available, and placed no restrictions on when she could cash it, the gift is complete for 2024 tax purposes regardless of when she actually deposits it in January. I'd suggest keeping a simple note in your records mentioning that the deposit delay was due to holiday bank closures - not required, but it provides helpful context if the timing ever comes up in the future. The most important thing is that you have documentation showing when you actually gave her the check, which it sounds like you do. You're well within the bounds of what the IRS considers "reasonable time" for cashing a gift check, so you should be all set to count this toward your 2024 annual exclusion limit!

This has been such a comprehensive discussion! As someone who's made similar year-end gifts before, I can confirm that your $17,000 check definitely counts toward your 2024 exclusion since you delivered it with adequate funds and no restrictions. One thing I haven't seen mentioned yet is that you might want to give your niece a heads up about the timing if she's not already aware. Sometimes recipients don't realize that holding onto gift checks for too long could potentially create complications, even though a few weeks is totally fine. Just a simple "hey, when you get a chance to deposit that check in January, that would be great" text can help ensure everything goes smoothly. Also, this situation is actually a perfect example of why some people prefer making electronic transfers for large gifts - no worries about banking hours or check-clearing delays. Though obviously that requires the recipient to be set up for electronic transfers, which isn't always practical for every situation. You handled this exactly right, and the documentation suggestions from others in this thread are spot-on for future reference!

I've been lurking on this thread for a while dealing with my own Error Code 101 nightmare, and I'm amazed at how many different root causes everyone has discovered! This has been like a masterclass in EIN application troubleshooting. After reading through all these solutions, I want to add one more potential cause that I discovered through trial and error: address formatting issues. I was getting Error 101 consistently even after trying the browser fixes, checking for old applications, and verifying my SSN records were clean. Turns out the problem was that I was entering my address exactly as it appears on my driver's license, which includes "Apt 4B" in the address line. But apparently the IRS system is very picky about how apartment/unit numbers are formatted. When I changed it from "123 Main St Apt 4B" to "123 Main St #4B" (using the pound symbol instead of "Apt"), the application finally went through. The IRS agent I eventually spoke with mentioned that their system has specific formatting requirements for addresses, especially for apartments, suites, and PO boxes. She said using abbreviations like "Apt," "Suite," or "Unit" sometimes causes validation errors, but symbols like "#" or "Ste" work better. Just another thing to add to the growing checklist of potential Error 101 causes! It's crazy how many tiny details can trip up this system. Thanks to everyone who contributed to this thread - you've created an incredible troubleshooting resource!

Wow, this thread has become an incredible resource for troubleshooting Error Code 101! As someone who just successfully got my EIN after dealing with this same error for almost two weeks, I wanted to add my experience to help others. In my case, it was actually a combination of issues. First, I had the address formatting problem that Mateusius mentioned - I was using "Unit 12" instead of "#12" which was causing validation errors. But even after fixing that, I was still getting Error 101. The second issue was that I had accidentally selected the wrong state in the "principal business location" field. I live right on the border between two states and put my mailing address state instead of where my business is actually physically located. The IRS system apparently cross-references multiple pieces of information for consistency, and this mismatch was triggering the error. What finally helped me figure this out was keeping a detailed log of each attempt (as Carmen suggested earlier) and changing only ONE thing at a time. When I fixed the address formatting but still got the error, I knew to look for other inconsistencies in my application. For anyone still struggling: I'd recommend creating a checklist based on all the solutions in this thread and working through them systematically. Also, print out your application before submitting so you can review every single field for potential formatting or consistency issues. Sometimes a fresh pair of eyes can spot mistakes you've been overlooking! This community has been incredibly helpful - thank you all for sharing your experiences and solutions!

I'm seeing a lot of complicated answers here but it's actually pretty simple. I've owned 3 homes and here's what I've learned: if you didn't pay it, you don't deduct it. The seller credit on closing is just an adjustment to make the sale fair - it's not income and it's not a deduction. When you actually pay the property taxes in 2025, that's when you deduct them - regardless of what period they cover.

As a first-time homeowner myself, I went through this exact confusion last year! You're absolutely right - since you didn't make any actual property tax payments in 2024, there's nothing to deduct on your 2024 return. The key thing to remember is that property tax deductions are based on the cash basis - meaning you can only deduct what you actually paid out, not what was assessed or owed. That seller credit you received at closing isn't taxable income to you, it's just an adjustment to make the transaction fair since you'll be paying the full year's taxes when they come due. When February 2025 rolls around and your escrow company pays those property taxes, you'll be able to deduct the full amount on your 2025 tax return. Keep your escrow statements and closing documents organized - you'll need them to show exactly what was paid and when. One tip: make sure to review your mortgage servicer's annual escrow analysis statement early next year. It will show exactly when property tax payments were made, which is crucial for determining the correct tax year for your deduction.