Slight tangent but might be useful - watch out for the "substantially equal periodic payments" rule getting confused with the rollover rule. My advisor messed this up for me. I thought I could take out regular payments from my IRA without penalty using the 72(t) SEPP program AND do a 60-day rollover in the same year. Turns out doing a rollover terminates your SEPP plan and triggers penalties on ALL previous distributions. Cost me thousands in surprise taxes. Just mentioning this because sometimes when people are looking at ways to access retirement funds early, these different rules get mixed up.

Great question about Roth IRA rollovers! I've been through something similar and learned the hard way about the complexity of these rules. One important detail I haven't seen fully addressed - when you withdraw from a Roth IRA, the IRS considers withdrawals to come from contributions first (FIFO - first in, first out). So if you've contributed $20,000 over the years and your account is worth $25,000, your first $20,000 withdrawn would be considered contributions and wouldn't face the 10% penalty regardless of the rollover. However, once you hit the earnings portion (that $5,000 in my example), those ARE subject to the 10% penalty if you're under 59½ - unless you complete a valid 60-day rollover or qualify for an exception. The tricky part with your dual withdrawal scenario is that even if both withdrawals combined stay within your contribution basis, you still can only do ONE rollover per 12-month period. So if something goes wrong and you can't complete the rollover for any reason, you'd want to make sure your total withdrawal amount doesn't exceed your contribution basis to avoid penalties on earnings. I'd strongly recommend getting documentation from your IRA custodian showing exactly how much you've contributed versus earned before making any withdrawals. This gives you a clear picture of your penalty-free withdrawal capacity.

The most important thing here is to just file ASAP! I put off filing late once and it only made the penalties worse. Even if you can't pay what you owe right now, file the return anyway and then set up a payment plan.

Just want to add some reassurance here - I was in the exact same situation two years ago and it really wasn't as bad as I thought it would be. Filed about 3 weeks late using TurboTax (similar to FreeTaxUSA) and the whole process was identical to filing on time. The key things that helped me: 1) File for tax year 2023 (not 2024), 2) E-filing still works normally even after the deadline, and 3) If you're getting a refund, you won't face penalties - just a delayed refund. I ended up owing about $200 and the penalty was only around $15 total. Way less scary than I'd built it up in my head! The IRS even sent me a clear breakdown of exactly what the penalty was for. Don't beat yourself up about it - life happens and this is more common than you think. Just get it filed in the next few days and you'll be fine!

Has anyone used H&R Block's expat tax service? I'm in a similar situation (US citizen in Auckland) and wondering if they're any good for international situations. Their regular service messed up my taxes before I left the States so I'm hesitant, but they advertise an expat specialty service.

I went through this exact same situation last year! The key thing to remember is that the US tax year mismatch with NZ isn't as complicated as it seems - you just report your NZ income earned during the US tax year (Jan-Dec 2023) on your US return. A couple of practical tips from my experience: 1. Keep detailed records of your income from both countries with dates - this makes everything easier 2. The Foreign Tax Credit can be really valuable, but you'll want to calculate whether that or the Foreign Earned Income Exclusion gives you better tax savings 3. Don't forget about potentially reporting any NZ bank accounts on your FBAR if the total exceeds $10,000 at any point during the year One thing I wish I'd known earlier - make sure you understand NZ's tax residency rules too. Since you qualify as a tax resident there, you'll need to report your US income on your NZ return as well. The timing can get tricky since you might file your US return in April but your NZ return isn't due until July. If you're comfortable with TurboTax, their Premier version handles foreign income reporting pretty well. Just make sure you have all your NZ pay slips converted to USD using the proper exchange rates for when you earned the income.

Based on all the discussion here, I'd definitely echo getting professional help given the IRS scrutiny on conservation easements. One thing I haven't seen mentioned yet is making sure your land trust is a qualified organization under IRC 501(c)(3) - the IRS has been challenging deductions where the receiving organization didn't meet all requirements. Also, Diego, regarding your valuation concern - if your property is near a growing suburb, you might want to look into whether any zoning changes or development plans are in the works for your area. Sometimes local planning departments have information about future growth that could significantly impact your property's development value. An appraiser experienced with conservation easements in your region would know to research these factors. Don't rush the amendment - better to take time now to get everything right than deal with an audit later. The three-year window gives you plenty of breathing room to do this properly.

Diego, I'd definitely recommend getting that second appraisal opinion before filing your amended return. Given that your property is near a growing suburb, $78k for 45 acres with development potential does seem potentially undervalued. I've seen similar situations where the initial appraiser didn't fully account for future development rights or subdivision potential. The key is finding an appraiser who specifically specializes in conservation easement valuations - they understand the "before and after" methodology required by the IRS and know how to properly research zoning, future land use plans, and comparable sales of development rights in your area. Since you have three years to amend, I'd suggest this order: 1) Get a consultation with a tax attorney who handles conservation easements, 2) If they recommend it, get that second appraisal, 3) Review all your documentation against IRS requirements, then 4) File the amended return with confidence. Your situation sounds completely legitimate since it's genuine family land preservation, but the IRS scrutiny means the documentation has to be perfect. Taking the time to get professional guidance upfront will likely save you significant stress and potential audit issues later.

Pro Series crashes CONSTANTLY during peak season!!! Don't believe the hype. I lose at least an hour of productive time every day dealing with software glitches. Look at ATX instead if ur doing mostly simple returns.

I'm a CPA who switched to Pro Series two years ago and have mixed feelings. The software itself is solid for basic to moderately complex returns - handles most situations you'll encounter with individual and small business clients well. The interface is intuitive once you get used to it, and the diagnostic tools are helpful for catching errors. However, I have to echo some concerns about stability during peak season. I've experienced crashes during high-volume periods, though not as frequently as Katherine mentioned. The key is saving your work frequently and having good backup procedures. For 25 returns, the pay-per-return pricing Connor mentioned could definitely work in your favor. Just factor in the potential learning curve time if you're switching from another platform - plan to start early in the season to get comfortable with the workflow before things get hectic. One tip: if you do go with Pro Series, invest in a solid internet connection and consider having Claimyr or similar service ready for tech support issues during busy periods. The combination can make the experience much smoother.