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One thing nobody has mentioned - make sure you have enough earned income to support your IRA contributions! Since you're retired with only part-time work, you need at least $15,000 in W-2 wages to max out contributions for both you and your wife ($7,500 each if you're over 50). The Roth conversion income doesn't count as "earned income" for IRA contribution purposes. Only wages, self-employment income, and a few other types of income qualify.
That's a really important point I hadn't considered! My part-time job pays about $25,000 per year, so I should be covered for both our contributions. Does alimony count as earned income too? I have a small amount of that coming in as well.
Alimony is actually a bit complicated. If your divorce agreement was finalized before 2019, then alimony you receive counts as earned income for IRA contribution purposes. If your divorce was finalized in 2019 or later, then alimony is no longer considered earned income for IRA contributions (or taxable income for you at all). But with $25,000 from your part-time job, you've definitely got enough earned income to max out both IRA contributions regardless of the alimony situation.
Has anyone actually tried doing exactly what the original poster is asking about? I'm in an almost identical situation (part-time job, not eligible for their 401k, doing a large Roth conversion), and my tax software flagged my IRA deduction when I entered the Roth conversion amount.
Which tax software are you using? I had the same issue with TurboTax but it was actually a false flag. When I continued through the process and indicated I wasn't eligible for my employer's plan (despite my employer having one), it eventually calculated the correct deduction. Some tax software gets confused by this scenario initially but sorts it out when you complete all the retirement questions. It's definitely worth double-checking your W-2 to make sure box 13 isn't checked.
Honestly with all those different forms and income sources, you should definitely hire someone this first time. I tried doing mine myself last year with multiple 1099s and crypto and ended up missing a bunch of deductions. Paid an accountant this year who found like $2,800 more in refunds than I would have gotten doing it myself. Ask friends for recommendations for accountants who work with younger people/first time filers. Many offer student discounts. And the money you spend will likely be saved in either reduced tax liability or avoiding penalties for mistakes.
How much did it cost you to hire an accountant? That's my concern - I'm on a pretty tight budget.
I paid $275 for my tax preparation, but my situation was pretty complex (multiple states, business income, investments). For your first-time filing with a somewhat simpler situation, you might find someone for $150-200. Some accountants also offer sliding scale fees for students or first-time filers. The value really comes from learning how everything works so you can potentially do it yourself in future years. Ask them to explain what they're doing as they go, and take notes about which forms apply to your situation. Consider it both a tax service and an education investment.
If your income isn't crazy high, check if there's a VITA (Volunteer Income Tax Assistance) program near you. They do free tax prep for people making under $60k. I used them when I was in college and they handled my W-2s, 1098-T, and even some basic investment stuff. Not sure about crypto though.
VITA is great but sometimes they won't help with self-employment (the 1099 stuff) or more complex situations. Worth checking though since each location has different capabilities.
Another option to consider is a 1031 exchange if you want to invest in another rental property instead of taking the capital gains hit. You can defer all the capital gains, though you'd still have to pay the depreciation recapture. I did this with a property last year - sold my rental and rolled all proceeds into a new investment property. The key is you need to identify the replacement property within 45 days and close within 180 days. And you need to use a qualified intermediary to hold the funds between sales.
Thanks for mentioning the 1031 exchange option. I had considered that briefly but wasn't sure if it would work in my situation since I'm planning to move back into the property first. Would moving back in disqualify it from a 1031 exchange later? Or would I need to keep it as a rental the whole time?
Yes, moving back in would complicate things for a 1031 exchange. For a property to qualify for a 1031 exchange, it needs to be held for productive use in a trade or business or for investment purposes at the time of the exchange. If you convert it back to your primary residence, it no longer qualifies as investment property. So if you want to do a 1031 exchange, you'd need to sell it while it's still a rental property. Once you move back in, that option is effectively off the table.
One thing nobody's mentioned yet - if you claimed any rental losses during those 3 years when it was a rental property, check if any of those were suspended passive losses. When you sell the property, you can use those suspended losses to offset some of the gain or recaptured depreciation. This caught me by surprise when I sold my rental last year - had about $8k in suspended passive losses from years where my income was too high to claim the rental losses, and my accountant was able to apply those against my depreciation recapture amount.
A quick tip that helped me with a similar issue - request your "Account Transcripts" directly from the IRS before filing any amendments. These will show how your business is classified in their system. You can get these online through the IRS website by creating an account at https://www.irs.gov/payments/view-your-tax-account. The transcript will show if you're on record as an S-corp or LLC, which helps confirm whether your election was properly processed. This saved me a ton of headache because I could prove to my new accountant that the S-corp election was in the IRS system even though my old preparer had been filing incorrectly.
Does anyone know if the transcripts also show if you've been assessed penalties for filing under the wrong business type? Or would those just appear as general penalties without specifying the reason?
The account transcripts generally don't specify the exact reason for penalties, they just show the penalty amount, code, and date assessed. However, you would see if there were any penalties at all, which might help you understand the full financial impact of the incorrect filings. If you need to know specifically why a penalty was assessed, you would need to request a call with the IRS (Claimyr mentioned above can help with this) or request a detailed explanation of penalties in writing, which takes much longer to receive.
Quick warning based on personal experience - when you amend from LLC to S-corp returns, make sure your new preparer correctly handles any state tax implications too. I fixed my federal returns but completely overlooked that my state returns also needed to be amended to match the corrected filing status. Ended up with a mess at the state level when they couldn't reconcile my federal and state filings. Some states also have different rules for S-corps vs LLCs, so you might have overpaid state taxes too that could be refundable.
Omar Mahmoud
Another option nobody's mentioned yet - if you used an IP PIN last year, check your old tax return! Your previous year's tax software might have saved a copy of the form with your IP PIN on it. I lost mine last year and nearly panicked until I realized I had a saved PDF of my entire return from the previous year which included the IP PIN letter. Might be worth checking your email for tax receipt confirmations too - sometimes they include that info. If that doesn't work, definitely try the specialized unit number (800-908-4490) that someone mentioned above - they're usually more accessible than the main IRS lines.
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Chloe Harris
ā¢This is great advice! I just checked my old emails and found my TurboTax confirmation from last year which had my IP PIN information in the attached PDF. Saved me so much hassle! Definitely check your email archives before going through the whole recovery process.
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Diego Vargas
Has anyone had success getting their refund without the IP PIN? I'm wondering if I can just file without it and explain the situation on the return somehow? I'm worried my stimulus money will go to someone else if I don't file soon.
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NeonNinja
ā¢DO NOT file without your IP PIN if you've been issued one! The IRS automatically rejects returns filed with your SSN that don't include the correct IP PIN. It triggers their fraud detection system and can cause even bigger delays and potential audits. Always get a replacement PIN through the proper channels before filing.
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