When I had both W2 and 1099 income, I learned that if you physically go to an IRS Taxpayer Assistance Center, they sometimes offer free tax prep services if your income is below certain limits. You need to call to make an appointment though. Also check if your local library or community center offers VITA (Volunteer Income Tax Assistance) services. They'll do your taxes for free including Schedule C if your income is under about $60k.

Just to add another perspective - I had a very similar situation with W2 income from two states plus freelance 1099 income. After trying multiple free options, I ended up going with H&R Block's online service. They have a mid-tier option that handles both W2 and Schedule C filing for around $50, which was way cheaper than their in-person service. What really helped me was their interview-style questions that walked me through the multi-state income reporting step by step. They automatically calculated how much state tax I owed to each state based on where I earned the income, which was exactly what I needed for my Colorado/Nevada situation. The key thing I learned is that while you definitely can't split your filing like you originally asked, there are affordable options beyond the expensive TurboTax upgrades. Don't feel like you're stuck paying premium prices just because you have mixed income sources!

One important consideration that hasn't been fully addressed is the impact of state residency changes over time. If you're setting up 529 plans for multiple generations, family members may move between states, which can complicate the tax benefits and penalties. I learned this the hard way when my daughter moved from our home state (which offered tax deductions for 529 contributions) to a state that taxes 529 earnings differently. We had to navigate not only the original state's recapture provisions but also understand how her new state would treat distributions. Additionally, for those considering this as a long-term wealth transfer strategy, keep in mind that tax laws can change significantly over decades. The current favorable treatment of 529 plans isn't guaranteed forever. Congress has modified 529 rules several times since their creation, and there's always the possibility of future changes that could affect multi-generational planning strategies. That said, even with these risks, 529 plans remain one of the most flexible tax-advantaged vehicles available for education savings and wealth transfer, especially when combined with the expanded qualified expense categories from recent legislation.

Great discussion everyone! I've been using 529 plans for wealth transfer for about 8 years now and wanted to share some practical insights from experience. The strategy definitely works, but I've learned a few things the hard way: 1. **Documentation is crucial** - Keep meticulous records of all beneficiary changes, contribution sources, and the reasoning behind transfers. The IRS may scrutinize patterns that look like you're primarily using 529s for wealth transfer rather than education. 2. **State tax arbitrage opportunities** - Some states (like Nevada, Utah, and New Hampshire) offer excellent 529 plans with no residency requirements and favorable tax treatment. You don't have to use your home state's plan, especially if it has high fees or limited investment options. 3. **Gift tax coordination** - Remember that each spouse can contribute separately, effectively doubling your annual exclusion amounts. My wife and I can jointly contribute $36,000 per beneficiary annually without gift tax implications, or $180,000 using the 5-year front-loading election. 4. **Consider Roth conversions alongside this strategy** - While you're building up 529 balances for the next generation, converting traditional IRA funds to Roth IRAs can complement the tax-free growth strategy, especially in lower-income years. The math really does work in your favor with a long enough time horizon, but don't put all your eggs in one basket. Legislative changes are always possible, and having multiple wealth transfer vehicles provides more flexibility.

I've been lurking in this thread for days and I have to say, this community has accomplished something incredible here. You've basically created the most comprehensive guide to actually reaching the IRS that I've ever seen anywhere online! I'm dealing with my own payment nightmare - my April automated payment of $203 got processed by my bank but isn't showing up in the IRS system at all. After reading through everyone's detailed success stories, I feel like I actually have a real strategy now instead of just randomly dialing and hoping. The pattern is so clear: collections number (800-829-0922), early morning calls around 8:30 AM on weekdays, have all documentation ready, and mention the "reconciliation queue" issue upfront. It's amazing how consistent the success rate has been once people started using this approach. What really strikes me is how the IRS agents like Patricia seem to immediately understand the problem once you mention the March/April processing issues. It sounds like they're very aware of these system glitches but there's just no official communication about it to taxpayers. I'm planning to call Monday morning with my bank statements and payment confirmations organized. After seeing so many people get their issues resolved in 15-25 minutes once they reach the right department, I'm cautiously optimistic this won't turn into a multi-week ordeal. Thank you to everyone who shared their experiences and strategies - you've turned what felt like an impossible bureaucratic maze into a solvable problem with clear steps. This thread should honestly be pinned somewhere as a resource for anyone dealing with IRS payment issues!

I just wanted to add my voice to this incredible thread! I've been dealing with a missing payment issue for my installment agreement - my February payment of $245 shows as processed by my bank but disappeared completely from the IRS system. I've been getting penalty notices even though I know I paid on time. After trying the main IRS number three times this week with zero success (those automated loops are truly maddening), I decided to try the collections number (800-829-0922) that everyone has had such success with. I called this morning at 8:25 AM and got through to an actual human being in just 16 minutes! The agent (Maria) immediately knew what I was talking about when I mentioned the payment processing issues from earlier this year. She said "Oh, you're probably dealing with our system update backlog" and was able to locate my payment in what she called the "unpostable transactions queue" within minutes. She processed the correction while I was on the phone and sent me an email confirmation with a case reference number. The whole call took about 20 minutes total. I honestly can't believe how smooth it was after expecting hours of frustration. This community has literally saved my sanity and probably hundreds of dollars in penalties. The strategy of calling early, having documentation ready, and using the specific terminology about processing queues made all the difference. Thank you to everyone who shared their experiences - you've created the best IRS phone system guide that exists anywhere!

Don't forget about the tax implications! If that final RMD went into her account after death, someone still has to pay taxes on it. If it goes to the estate, the estate will pay the taxes. If it goes back to the IRA and then to you as beneficiaries, you would report that distribution on your tax returns. Either way, the custodian will issue a 1099-R for that distribution. Make sure it's issued correctly depending on how you resolve this - to either the estate's tax ID or to you and your brother's SSNs if you're able to have the distribution redirected.

I went through something very similar with my father's IRA last year. One thing that really helped was getting everything documented in writing from the IRA custodian before making any decisions. When I called them, I specifically asked for written confirmation of: (1) the exact date the RMD was processed, (2) whether my dad had already satisfied his annual RMD requirement before his death, and (3) what their standard procedure is for handling distributions that occur after the account holder's death. Having that documentation was crucial when working with the estate attorney and the bank. The custodian actually admitted they shouldn't have processed the RMD after the death date and helped us reverse it back to the IRA so it could be properly distributed to the named beneficiaries. Also, don't wait too long on this - there are time limits for correcting these kinds of errors. Most custodians are pretty helpful once they understand the situation, but you need to act quickly while the paperwork trail is still fresh.

You might also want to check if you need to make an estimated tax payment this quarter rather than waiting until tax time. If you're normally a W-2 employee who gets refunds, you're probably fine waiting. But if this pushes your tax due over $1k for the year beyond what's being withheld, you might need to make an estimated payment to avoid an underpayment penalty.

Congratulations on your win! You've gotten some great advice here already. Just to add a bit more clarity - yes, you absolutely need to report this as "Other Income" on your tax return regardless of whether you receive a W-2G form or not. One thing I'd suggest is opening a separate savings account and immediately putting aside 25-30% of your winnings ($1,200-$1,440) for taxes. This covers both federal and state obligations and gives you a small buffer. It's much easier to do this now while you have the full amount than to scramble for tax money next April. Also, start keeping a simple log of any gambling activities for the rest of the year - both wins and losses. Even if you just buy a few lottery tickets or play bingo, track it all. If you itemize deductions, those losses can offset your winnings dollar-for-dollar up to the amount you won. The IRS considers all gambling winnings taxable income from dollar one, so there's no minimum threshold for reporting requirements on your end, even though there are thresholds for when organizations must issue forms to you.