I went through this exact same situation last year! The panic is real, but you're not alone in missing this filing requirement. Here's what I learned from my experience: First, yes you do need to file Form 5500-EZ for plan termination even though it's been 2 years. The IRS considers a rollover to an IRA as terminating the Solo 401k plan. Since your combined plan assets were around $270k, you definitely exceeded the $250k threshold that triggers the filing requirement. The good news is that the IRS has reasonable cause provisions for late filings, especially when you can demonstrate that the failure was due to circumstances beyond your control - like not being informed by your financial institutions about this requirement. When you file, include a detailed reasonable cause statement explaining exactly what happened: the TD Ameritrade acquisition, Schwab's inability to support Roth 401ks, and the fact that neither institution informed you of the 5500-EZ requirement. Document everything with dates and reference any correspondence you had with them. I also recommend checking if you qualify for the DOL's Delinquent Filer Voluntary Compliance Program (DFVCP), which often results in reduced penalties for good faith late filers. Don't wait any longer though - the penalties do continue to accrue, and voluntary compliance always looks better than being contacted by the IRS first.

I'm going through the exact same situation right now - rolled over my Solo 401k in 2023 and just discovered the Form 5500-EZ requirement. The stress is absolutely overwhelming! What really helped me was talking directly to an IRS agent who specializes in retirement plans. They explained that the key is demonstrating "reasonable cause" - which you clearly have since neither TD Ameritrade nor Schwab informed you of this requirement during the rollover process. The agent told me that institutional failures to provide proper guidance is actually one of the stronger reasonable cause arguments they see. Make sure to gather all your documentation from the rollover process - any emails, account statements, or paperwork that shows the institutions guided you through the process without mentioning Form 5500-EZ. The IRS agent I spoke with said this type of documentation significantly strengthens your case for penalty relief. Also, don't let the 2-year delay add to your panic. While it's not ideal, the agent mentioned they regularly process late filings that are much older, especially when there's clear reasonable cause. The important thing is getting it filed as soon as possible with a thorough explanation of the circumstances. You've got this - the situation is fixable and you're definitely not the first person to be caught off guard by this requirement!

One more thing to consider - check if your area has any rural development grants or infrastructure improvement programs available. Many counties and states offer cost-sharing programs for rural road improvements, especially if multiple property owners participate. I found out about a USDA Rural Development grant that covered 40% of our road improvement costs when we went through a similar situation. We had to form a small road association with our neighbors and apply as a group, but it saved us thousands. The application process took about 6 months, but it was worth the wait. Also, some utility companies will contribute to road improvements if they need better access for maintenance - worth asking your electric, gas, or phone companies if they'd be interested in cost-sharing since better road access benefits their service capabilities too.

Great question about rural road improvements! I've dealt with similar situations professionally, and there are definitely some key steps to follow. First priority is determining road ownership through your county recorder's office - this is absolutely critical before spending any money. Many rural roads exist in legal gray areas where ownership isn't clearly defined, which can create huge problems later. For tax implications, if you own the road section, the paving cost gets added to your property's tax basis (helpful when you sell), but won't give you an immediate deduction. However, there's one exception many people miss - if you use part of your property for business purposes (home office, rental, etc.), a portion of road improvements might qualify as a business expense. You'd need to work with a tax professional to calculate the business-use percentage. Also consider getting multiple quotes - $15,000 for 1/4 mile seems reasonable for basic asphalt, but prices vary wildly based on access, prep work needed, and local contractors. Some areas offer chip seal as a middle ground between gravel and full asphalt that costs about 40% less. Finally, document everything meticulously if you proceed - photos, contracts, receipts, property surveys. This documentation will be essential for tax basis calculations and potential future property disputes.

I dealt with a similar situation after Hurricane Laura damaged my roof and garage. One thing that really helped my case was getting a "scope of loss" document from a public adjuster who reviewed what my insurance company missed or undervalued. Even though I had to pay the adjuster, it was worth it because they found an additional $12k in damages that insurance initially overlooked. For your chimney situation, you might want to consider getting a structural engineer's assessment showing that removing the chimney versus rebuilding it creates a permanent decrease in your home's structural integrity and value. This could strengthen your FMV decrease argument beyond just the aesthetic/functional loss. Also, don't forget that you can deduct the cost of temporary protective measures you took immediately after the hurricane (like tarping, boarding up windows, etc.) as part of your casualty loss. These often get overlooked but they're legitimate disaster-related expenses. Just make sure everything was within a reasonable timeframe after the federally declared disaster.

I went through a very similar situation after Hurricane Michael hit our area. One crucial detail that hasn't been mentioned yet - make sure you understand the timing rules for casualty loss claims. Since yours was a federally declared disaster, you actually have the option to claim the loss on either your 2024 return (the year it happened) OR amend your 2023 return to claim it there, which could get you a refund faster. The key documentation you'll need beyond what others have mentioned is a detailed timeline showing when the damage occurred, when you received the insurance settlement, and when you made the decision to go with the wall replacement instead of full chimney rebuild. The IRS wants to see that you made reasonable efforts to restore the property but were financially unable to do so. For your specific situation with the chimney-to-wall conversion, I'd strongly recommend getting an appraisal or real estate professional's written opinion on how this impacts your home's resale value. A missing chimney can affect both the aesthetic appeal and functionality (no fireplace option for future buyers), which supports your FMV decrease calculation. One last tip - if you're planning to sell your home within the next few years, keep all this casualty loss documentation. It could affect your capital gains calculation since the casualty loss reduces your home's adjusted basis.

This is exactly why I always check for any processing issues before filing. H&R Block should have notified clients about this upfront - it's pretty frustrating to find out after the fact that your refund timeline just got extended by 1-2 weeks. At least now we know what's going on though. Thanks for sharing this info!

Same thing happened to me! Filed through H&R Block online on Jan 28th and was wondering why my state refund was taking so long. Really wish they had communicated this issue better - I only found out about the paper check thing when I called their customer service line yesterday. At least now I know to keep an eye on my mailbox instead of checking my bank account every day 📬

One thing to keep in mind is that most RSUs are taxed at vesting (your company probably withheld shares for taxes when they vested). So your actual cost basis for tax purposes is the FMV on vesting date, not zero. This means your older RSUs that are "lower than current price" might actually represent a loss if the current price is lower than when they vested! In that case, selling them would give you a capital loss you can use to offset other gains. Check your vesting statements carefully!

Great advice from everyone here! One additional consideration for @Kristin Frank - if you're in a higher tax bracket this year but expect to be in a lower bracket next year (maybe due to job change, retirement, sabbatical, etc.), it might make sense to delay selling the older RSUs to take advantage of the lower long-term capital gains rate when your overall income is lower. Also, don't forget about the Net Investment Income Tax (NIIT) - if your modified adjusted gross income exceeds $200K (single) or $250K (married filing jointly), you'll pay an additional 3.8% tax on investment income including capital gains. This could influence the timing of when you sell. The tools others mentioned like taxr.ai sound really helpful for modeling different scenarios, especially when you factor in state taxes and these additional considerations!