I'm so sorry for your loss, Liv. I went through this exact situation when my uncle passed away last year, and the whole certified copy vs transcript confusion is incredibly frustrating when you're already dealing with so much. One thing I wish someone had told me upfront: make sure to send your Form 4506 package via certified mail with return receipt requested, and keep the tracking number. The IRS processing centers can be slow to acknowledge receipt, and having that proof of delivery gave me peace of mind during the long wait period. Also, I'd recommend setting up a simple calendar reminder system for yourself. Mark the date you mail everything, then set reminders at 30 days, 60 days, and 70 days to check on status if needed. The waiting is agonizing when you're trying to settle an estate, but having those check-in points helped me feel more in control of the process. All the advice here about Form 4506 (not 4506-T), Form 56, and the $43 fee per year is spot-on. The hardest part really is just getting through the wait, but everyone who follows the proper steps does eventually get their certified copies. You're asking all the right questions and you'll get through this.

I'm so sorry for your loss, Liv. I went through this exact same process when my mother passed away two years ago, and I completely understand how overwhelming it can feel when you're trying to navigate IRS requirements while grieving. Everyone here has given excellent advice about Form 4506 and the certified copy process. I wanted to add one more tip that helped me avoid a costly mistake: before you submit everything, double-check that your father actually filed a return for 2023. If he passed away early in 2024, his final return might not have been filed yet, which would mean there's no 2023 return on file with the IRS to certify. If that's the case, you might need to file his final return first (Form 1041 for the estate and possibly an amended 1040 for him personally) before you can request certified copies. Your probate attorney should be able to clarify what specific tax years you need and whether all the returns have actually been filed. Also, I'd suggest asking your attorney if they need certified copies of both federal AND state returns - some estate processes require both, and it's much easier to handle everything at once rather than discovering later that you need additional documentation. The process is definitely tedious, but you're asking all the right questions. Having a clear checklist and timeline like others have mentioned will help you stay organized during what's already a difficult time.

You might want to check if you qualified for any partial Roth contribution during those years instead of assuming you couldn't contribute anything. The income limits have a phaseout range where you can make reduced contributions. For 2017, the phaseout for single filers was between $118,000-$133,000. Unless you were completely above the upper threshold, you might have been eligible to contribute something.

This is a really helpful thread! I'm dealing with a similar situation but from 2020-2022. One thing I learned from my tax preparer is that you should also check if your employer offers a 401(k) - if you have workplace retirement coverage, it can affect your ability to deduct Traditional IRA contributions, which impacts the backdoor Roth strategy that people mentioned. Also, make sure to keep detailed records of everything when you're going through the correction process. The IRS may ask for documentation years later, and having your Form 5329s, withdrawal confirmations from Vanguard, and calculation worksheets all organized will save you major headaches if they ever audit this. One last tip - if you end up owing multiple years of the 6% excise tax, you can sometimes set up a payment plan with the IRS rather than paying it all at once. Just call them (or use that Claimyr service others mentioned) to discuss options.

Just a heads up that the person BUYING the property in this scenario also needs to consider tax implications. When my mom sold me her house below market value, I didn't have to pay gift tax (that was on her), but when I eventually sold the property years later, I had to use HER original basis for calculating capital gains, not the discounted price I paid. This is called "basis carryover" for related party transactions and it really surprised me at tax time.

One important thing I haven't seen mentioned yet is the timing aspect of getting your appraisal. The IRS expects the fair market value to be determined as close to the transaction date as possible. If you're using an appraisal that's several months old, they might question its validity, especially in a volatile real estate market. Also, make sure your appraiser knows this is for a family transaction that will likely involve gift tax reporting. Some appraisers will note this in their report and provide additional documentation about their methodology, which can be helpful if the IRS ever questions the valuation. I learned this the hard way when my first appraisal didn't have enough detail and I had to get a second one specifically for tax purposes. The key is having rock-solid documentation for every aspect of this transaction - the appraisal, the reasons for the below-market sale, and proper filing of all required forms. It's definitely worth consulting with a tax professional who has experience with family property transfers before you proceed.

This thread has been incredibly helpful! I'm dealing with a similar situation with my first rental property purchase from last month. One thing I'd add based on my research is that the IRS Publication 527 (Residential Rental Property) specifically addresses this "placed in service" concept. What I found particularly useful was the distinction between startup costs (which may need to be amortized over 15 years) versus ordinary repair expenses (which can be deducted immediately). For example, if you're fixing existing issues to make the property rentable, those are generally repairs. But if you're adding new features or significantly upgrading systems, those would be improvements. I've been keeping a detailed spreadsheet categorizing each expense and the reason for it (e.g., "Fixed leaky faucet in kitchen - necessary for property to be rentable" vs "Upgraded to granite countertops - improvement"). This level of documentation should help support my position if there are ever any questions. The timeline approach that several people mentioned here is spot-on. I started my "available for rent" marketing about 2 weeks after purchase, even though I knew I'd need another month of repairs. Having that documented intent to rent seems to be the key factor in establishing when the property is considered "in service.

I've been following this discussion as someone who just went through a similar situation with my rental property purchase earlier this year. One thing that really helped me was understanding that the IRS actually has different rules for different types of pre-rental expenses, and it's not just a simple "before vs. after" distinction. What I learned from my tax attorney is that there are essentially three categories of pre-rental expenses: 1. **Ordinary repairs to make property rentable** - These can usually be deducted immediately if you can show active rental preparation 2. **Capital improvements** - Must be depreciated over 27.5 years regardless of timing 3. **Business startup costs** - May qualify for immediate deduction up to $5,000 with remaining amounts amortized over 15 years For your $3,700 in repairs, the key question isn't just timing but also whether these expenses fall into category 1 or 2. Fixing roof leaks and patching drywall to restore the property to rentable condition would typically be category 1 (immediately deductible), while something like installing a new HVAC system would be category 2 (must be depreciated). The documentation strategies everyone mentioned here are crucial, but also consider getting a second opinion from a CPA who specializes in rental properties. Some general practice accountants tend to be overly conservative on rental property issues because they don't deal with them as frequently. I ended up saving about $1,800 in taxes by properly categorizing my pre-rental expenses instead of capitalizing everything my original accountant suggested.

My CPA told me that the hobby loss presumption kicks in after 3 years of losses, but you get 5 years for activities involving horses (weird exception lol). For your YouTube channel, document EVERYTHING that shows you're trying to make money. Schedule C should show increasing income even if expenses are higher.

One thing I haven't seen mentioned yet is that the IRS also considers the "manner in which you carry on the activity" as one of the nine factors. For YouTube creators, this means treating your channel like a real business - having a content calendar, tracking analytics, actively seeking sponsorships, and reinvesting profits back into the channel. I'd recommend keeping a business journal documenting your efforts to monetize and grow the channel. Note down networking activities, market research, content strategy changes, etc. This creates a paper trail showing you're genuinely trying to build a profitable business, not just pursuing a hobby that happens to make some money. Also, don't artificially limit your legitimate business expenses just to show a small profit. The IRS would rather see realistic business operations than obvious manipulation of numbers. Focus on building a strong case for business intent through your actions and documentation.