Has anyone used the "reasonable basis" approach for this? My CPA told me that we could just use a reasonable method to allocate dividends for the fiscal year and document our methodology, without needing to get special reports.

I'm currently dealing with a similar situation for my grandfather's estate that has a fiscal year ending in August. One thing that's been helpful is creating a detailed spreadsheet tracking each dividend payment by month, security, and estimated classification based on the prior year's 1099-DIV percentages. For mutual funds specifically, I found that many fund companies publish monthly or quarterly tax estimates on their websites that can help bridge the gap until you get the official 1099s. Vanguard, Fidelity, and others often have detailed tax information available in their fund profiles. Also worth noting - if the estate has significant dividend income, consider making estimated tax payments quarterly to avoid underpayment penalties. The IRS doesn't care that you're waiting for complete documentation; they still expect timely payments based on reasonable estimates.

I'm dealing with something similar right now! My PTIN application has been stuck in "additional verification" for about 3 weeks, and it's so frustrating watching everyone else get approved instantly. One thing I discovered that might help - when you call the PTIN helpdesk, try calling right at 8:00 AM ET when they open. I had better luck getting through early in the morning versus later in the day when the lines are jammed. Also, I learned that you can actually fax your expedite request directly to the PTIN office at 855-215-6822. Sometimes faxed requests get processed faster than phone calls because they create a paper trail. Make sure to include your application number, explain the employment situation, and request expedited processing due to time-sensitive employment needs. The waiting is absolutely nerve-wracking, especially when you know your career opportunity is hanging in the balance. But from what I've read in this thread, it sounds like most people do get resolved much faster than the initial 6-week estimate once they start making the right calls. Hang in there!

I went through this exact same nightmare last year! The "random" additional verification is so frustrating when you're watching everyone else sail through the process. Here's what finally worked for me: I called the PTIN helpdesk (877-613-7846) at exactly 8:00 AM on a Tuesday morning and got through on the first try. The key phrase that seemed to get their attention was "employment-related hardship due to PTIN delay." I explained that I couldn't start my position without the PTIN and asked if there was any way to expedite based on employment necessity. The agent was actually really helpful once I got through to a real person. She looked up my application and found that one of my documents had been flagged for "illegible text" even though it looked fine to me. She was able to accept a new upload over the phone while I stayed on the line, and my PTIN was approved within 48 hours after that call. Also, make sure you're logging into your PTIN account online every day - sometimes the status changes there before you get any email notification. Don't give up! The 6-week timeline is worst-case scenario, and most employment-related expedite requests get resolved much faster once you get to the right person.

One thing nobody's mentioned: if you're expecting refunds for these years, you probably won't get interest on the 2020 and 2021 refunds because you filed more than 45 days after the due date. But for some reason the IRS has been adding interest to my 2022 refund even though I just filed it late last month. The interest rates are actually pretty decent too - like 5-7% depending on the quarter.

Don't panic! You're definitely not going to jail - the IRS is much more interested in getting their paperwork than punishing people who just got overwhelmed. I went through something similar a few years back. Since you mentioned you're W-2 only and likely owed refunds, you're in a pretty good position. The IRS doesn't penalize you for filing late when you're owed money. However, definitely prioritize getting that 2020 return filed ASAP since you only have until April 15th, 2024 to claim that refund. For gathering your documents, start by creating an account on IRS.gov and requesting your wage and income transcripts. This will show you all the W-2s, 1099s, and other tax documents that were filed with your SSN for each year. It's like getting a cheat sheet of what you need to report. You can absolutely use tax software for this - most companies like TaxAct, FreeTaxUSA, and TurboTax offer prior year versions. Just remember that 2020 and 2021 will likely need to be mailed in as paper returns, while 2022 can probably still be e-filed. Take it one year at a time, starting with 2020, and you'll get through this faster than you think!

Does anyone know if RSUs get reported on a 1099-B or just on the W-2? I've been getting conflicting information.

Welcome to the RSU club! One thing I wish someone had told me when I first got RSUs - consider the timing of when you might want to sell after vesting. Since the vested shares are already taxed as ordinary income at vesting, any future gains will be taxed as capital gains. If you hold for more than a year after vesting, you get the more favorable long-term capital gains rate instead of short-term (which is taxed as ordinary income again). Also, don't forget that RSUs can push you into a higher tax bracket in the year they vest, especially if you have a large vesting event. It might be worth talking to a tax professional about estimated quarterly payments if your regular paycheck withholding won't cover the extra tax burden from the RSUs.

One thing nobody's mentioned yet - when both spouses work, you might hit the "marriage penalty" depending on your income levels. Basically, if both of you make similar incomes, you could end up in a higher tax bracket than if you were single. However, if one spouse makes significantly more than the other (which might be the case at first if your wife is just returning to work), you might actually get a "marriage bonus" where you pay less than two single people would. Make sure whatever withholding calculator you use accounts for this. We got surprised with a $2,900 tax bill the first year both my wife and I worked full-time because our withholdings didn't account for the combined income pushing us into a higher bracket.

The marriage penalty typically affects couples where both spouses have similar moderate to high incomes. For 2024, it's most noticeable in the 22% and 24% tax brackets. If you're both making around $65K, you're definitely in the range where this can hurt. The penalty happens because the tax brackets for married filing jointly aren't exactly double the single brackets at higher income levels. For example, the 22% bracket for singles goes up to about $47K, but for married filing jointly it only goes up to about $89K (not $94K which would be double). A few strategies that can help: maximize your 401(k) contributions to reduce taxable income, consider if itemizing deductions makes sense now that you have two incomes, and definitely use the IRS withholding calculator or a tool like taxr.ai to make sure you're withholding enough throughout the year. The last thing you want is a surprise tax bill in April!