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Just to add another data point - I actually did exactly what you're describing about 2 years ago. I had approximately $215k in my Roth 401k (about $120k contributions) and rolled it to my existing Roth IRA which had about $35k (with $25k being contributions). After the rollover, my contribution basis was properly tracked as $145k total. I needed money for a medical emergency about 3 months later and was able to withdraw $52k without any tax consequences or penalties. The key is making sure your 401k plan administrator correctly reports the contribution portion of your rollover. My plan provided a statement breaking down the contributions vs. earnings portions, which I kept for my records. When I filed my taxes the following year, everything worked as expected - no issues.
That's really helpful to hear a real-world example! Did you have to do anything special on your tax return to document the rollover and subsequent withdrawal? And did your 401k plan administrator automatically provide that contribution/earnings breakdown, or did you have to specifically request it?
You'll receive a 1099-R from your 401k provider showing the total distribution, and you'll need to report the rollover on your tax return. For the withdrawal, you'll get a 1099-R from your IRA custodian the following year. I didn't need to file any special forms since my withdrawal was less than my total contributions, but I did keep detailed records of my basis. My plan administrator provided the contribution/earnings breakdown automatically as part of the distribution paperwork. If yours doesn't, definitely request it - you need this documentation to establish your basis. Some administrators have this readily available, while others might require you to specifically ask for a "distribution statement showing contribution and earnings portions.
One thing nobody has mentioned yet - while the ordering rules do work as everyone's described (contributions come out first), be careful about one detail: the timing! If you roll over your Roth 401k to a NEW Roth IRA (rather than one you've had for 5+ years), you might still face the 5-year rule on qualified distributions of EARNINGS. Contributions can still come out anytime, but if you're trying to access earnings within 5 years of establishing your FIRST Roth IRA, those earnings would be subject to tax/penalty even if you're over 59.5. The 5-year clock for earnings starts when you open your first Roth IRA, not when you do the rollover. This trips up a lot of people who wait until retirement to open their first Roth account.
Wait I'm confused. So if I open my first ever Roth IRA today at age 55, then immediately roll over my Roth 401k that I've had for 20 years, I still have to wait until age 60 to access the earnings tax-free even though I'll be past 59.5?
That's exactly right. The 5-year rule for Roth IRA earnings requires that your first Roth IRA was established at least 5 tax years ago AND you're 59½ or meet another exception (disability, first-time home purchase, etc.). So in your example, if you open your first Roth IRA at 55 and roll over your 20-year Roth 401k, you could access all the contribution portions immediately without tax or penalty. However, for the earnings to come out tax-free, you'd need to wait until both: 1) you're 59½ (which you already are), and 2) it's been 5 tax years since you established your first Roth IRA - so that would be at age 60.
Current landlord here (5 properties). One strategy that worked well for me was creating an LLC for my rental properties and electing S-Corp taxation. This allowed me to pay myself a reasonable salary with proper withholding while also taking distributions. It's definitely more complicated than just increasing your W-4 withholding, but it can potentially save you on self-employment taxes depending on your situation. Just something to consider if your rental business grows.
Doesn't creating an LLC and doing the S-Corp election cost a lot in administrative fees? I've heard you need to run payroll and everything. Is it really worth it for just one property?
You're right that it doesn't make financial sense for just one property. The administrative costs (state filing fees, payroll service, possibly a CPA) would likely outweigh the tax benefits until you have multiple properties generating significant income. For a single property, increasing your W-4 withholding or making quarterly estimated payments is definitely more cost-effective. I'd say the S-Corp approach usually starts making sense around 3-5 properties or when rental income exceeds about $40,000 annually. Until then, the simpler approaches others have mentioned are your best bet.
dont forget about depreciation! it will offset some of ur rental income. my first year as landlord i was worried about owing but the depreciation deduction was huge and actually cancelled out most of my rental profits for tax purposes. talk to a tax person about this.
This is really important. Depreciation is actually required by the IRS even if you don't claim it. And they'll hit you with depreciation recapture taxes when you sell regardless. So definitely claim it!
Just want to point out something important here - the "square footage" method is crucial if you go the home office route. Since you're using a substantial portion of your home (half of 9,000 sq ft!), you'd calculate the percentage of your home used for business and apply that to your home expenses. For example, if exactly half is used exclusively for the cat boarding business, you'd deduct 50% of your mortgage interest, property taxes, utilities, insurance, repairs, etc. For direct business expenses (like the cat condos or special flooring), those are 100% deductible regardless. Be super careful about claiming exclusive business use though. The space must be used ONLY for business. If you occasionally use the "cat area" for personal purposes, you could lose the entire deduction in an audit.
That exclusive use requirement is so tricky! I have a home daycare and the IRS has different rules specifically for daycare providers. We can claim spaces that have mixed use (like kitchen, bathroom) based on time used for business. I wonder if there's any similar exception for pet boarding? Might be worth looking into.
Here's something nobody's mentioned yet: if your LLC has been deducting rent payments to you, but those should have been treated as income subject to self-employment tax, you might have a tax liability for the difference plus penalties. Before you make any changes, you should calculate what the potential back taxes might be. Depending on how many years this has been going on and the amounts involved, it could be significant. Sometimes it's worth getting a third opinion from a tax professional who specializes in small business issues before making any drastic changes or amendments.
That's a really good point. Do you think I need to file amended returns for previous years? Or could I just start doing it correctly going forward? I'm a bit worried about opening a can of worms if I start amending returns.
Generally, if you discover an error on past returns, you should file amended returns. However, there's a 3-year statute of limitations on most tax issues, so you'd typically only need to amend returns from the past 3 years. That said, this isn't necessarily a black-and-white error. There are legitimate situations where rental arrangements between yourself and your business can be appropriate, especially if you have the right business structure. Before amending anything, I'd recommend getting that third opinion from someone who can look at your specific situation. If you do need to amend, a tax professional can help you present the changes in the most favorable light, possibly reducing or eliminating penalties. Sometimes when you self-disclose and correct issues, the IRS is more lenient than if they discover the issue during an audit.
One thing nobody mentioned yet - if you're considering an Offer in Compromise through the Fresh Start Program, be prepared for a VERY thorough financial investigation. They want bank statements, pay stubs, bills, asset values - basically your entire financial life laid bare. I went through this last year and while it was worth it (settled $32k in taxes for about $8k), it was also stressful and invasive. Just be prepared for that level of scrutiny if you go that route.
Did you use a tax professional to help with your Offer in Compromise or did you handle it yourself? I'm wondering if it's something I can navigate on my own or if I should budget for professional help.
I started the process myself but ended up hiring a tax resolution specialist about halfway through. The forms themselves aren't super complicated, but determining the right offer amount is tricky. The IRS rejected my first submission because I miscalculated my "reasonable collection potential." The professional helped me resubmit with the correct calculations and stronger documentation of my hardships. It cost me about $1,500 for their help, which felt worth it since they got my offer accepted. If your situation is straightforward you might be able to do it yourself, but having someone who knows what the IRS is looking for definitely improved my chances.
Don't forget that the Fresh Start Program also increased the tax lien threshold! The IRS won't file a Notice of Federal Tax Lien unless you owe more than $10,000 now (used to be much lower). That might help with your goal of buying a house eventually since tax liens can really mess with your ability to get financing.
TillyCombatwarrior
I see everyone suggesting the identity theft angle which is definitely possible, but there could be another explanation. The IRS sometimes makes major data entry errors. Last year they attached someone else's W-2 to my account by mistake - had a similar name but completely wrong SSN. Could be worth checking your Social Security statement online to see if there's any reported income from that employer there too. If it's not showing on your SS record but is on your IRS transcript, that strengthens the case that it's just an IRS error rather than actual identity theft.
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Nalani Liu
ā¢I hadn't even thought about checking my Social Security statement! Just logged in and interestingly there's no record of that employer or the $78k on my Social Security earnings record. Does that mean it's more likely just an IRS error than actual identity theft? Should I still follow all the identity theft steps everyone mentioned or is there a faster way to resolve this?
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TillyCombatwarrior
ā¢If it's not showing up on your Social Security earnings record, that's actually good news! It suggests it's more likely an IRS processing error rather than someone actually using your info to work somewhere. I'd still take precautions like monitoring your credit, but you might be able to resolve this more quickly by calling the IRS and specifically telling them it appears to be a processing error since the income doesn't appear on your Social Security record. Ask to speak with someone in the Wage and Income department rather than Identity Theft. In my case, they were able to remove the incorrect W-2 and release my refund within about 6 weeks of identifying the error. Still frustrating, but faster than the full identity theft resolution process!
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Anna Xian
Make sure you also check if the company actually exists! Google the company name, look them up on your state's business registry website, etc. I had a weird W-2 show up and spent weeks on the identity theft process only to discover the company was legitimate but had transposed some digits in the SSN they reported to the IRS. The fastest resolution came when I actually contacted the company's HR department directly. They were able to correct the error on their end and submit amended forms to the IRS.
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Jungleboo Soletrain
ā¢Smart advice! But how do you approach a company you've never worked for? I'm dealing with a similar issue and worry they'll just ignore me since I'm not an employee.
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