Great question! I was in a similar situation a few years ago. Here's how I think about it: If you're already at 15% for your 401k and getting your full employer match, the decision really comes down to your personal financial goals and cash flow needs. **Go with higher 401k contributions if:** - You're behind on retirement savings for your age - You have stable income and don't need the extra cash flow - You're close to a tax bracket threshold (as mentioned above) - You want to maximize long-term wealth building **Go with higher withholding if:** - You're on track for retirement but just want to avoid owing taxes - You might need more flexibility with your money during the year - You have other financial priorities (emergency fund, debt payoff, etc.) - You prefer having more control over your cash flow One middle-ground approach: increase your 401k by just 2-3% and adjust your withholding slightly. This way you get some additional tax reduction benefits from the 401k while not tying up too much extra cash. The most important thing is that you're being proactive about this instead of getting surprised again next April!

Another factor to consider is your current tax situation versus your expected tax situation in retirement. If you think you'll be in a lower tax bracket when you retire (which is common), then maximizing traditional 401k contributions now makes a lot of sense - you're getting a tax deduction at your current higher rate and will pay taxes later at a lower rate. However, if you expect to be in the same or higher tax bracket in retirement, or if tax rates in general go up by then, the immediate tax savings from higher 401k contributions might not be as beneficial long-term. Given that you're already at 15% which is really solid, and you owed taxes this year, I'd lean toward a hybrid approach: bump your 401k up to maybe 17-18% and also increase your withholding slightly. This gives you some additional tax reduction benefits while also ensuring you don't owe next year. The IRS penalty for underpaying can be pretty steep if you owe more than $1,000, so making sure you're covered on the withholding front is important regardless of what you do with your 401k.

One important thing to watch for with multiple W2s - Social Security tax. Each employer withholds 6.2% of your wages for Social Security up to the annual wage limit ($147,000 for 2022). If your combined income from both jobs exceeded that limit, you may have overpaid Social Security tax that you can get back when filing.

Just wantd to mention, when I had 2 w2s I just added the box 1 income from both, added the fed witholding together, and the state witholding together. Enter those on your 1040 and ur good to go! No need to complicate it imo.

Don't overthink this. The property is still a rental until you sell it. Expenses still go on Sch E. If you get audited, the IRS isnt gonna care that it was vacant while u were trying to sell it. Happens all the time.

I went through this exact situation two years ago with a duplex that sat vacant for 5 months while trying to sell. What really helped me was creating a clear paper trail showing my intent to sell rather than abandon the property. I kept copies of all MLS listings, price reduction notices, showing feedback, and even rejection letters from potential buyers. When I filed my Schedule E with expenses but no rental income for those months, I included a brief statement explaining the vacancy was due to active marketing for sale. The IRS never questioned it, but having that documentation gave me peace of mind. Also, make sure you're only deducting expenses that you would have paid anyway as a rental property owner - don't try to deduct any costs specifically related to marketing the property for sale, as those should be treated as selling expenses when you calculate capital gains. One tip: if you're doing any repairs or improvements to help with the sale, be careful how you categorize those. Minor repairs to maintain the property can still go on Schedule E, but major improvements to increase sale value should be added to your basis.

One thing to consider that hasn't been mentioned yet - if you do decide to get married, make sure to update your W-4 withholdings at work! Many couples forget this step and end up owing money at tax time or getting a huge refund (which means you gave the government an interest-free loan all year). With your combined income of $120,000 and a baby on the way, your tax situation will be quite different than when you were both single. The IRS has a good withholding calculator on their website, or you can use the new W-4 form which has been redesigned to be more accurate for married couples. Also, don't forget about Dependent Care FSA if either of your employers offers it - you can set aside up to $5,000 pre-tax for daycare expenses once the baby arrives. This is separate from the child care tax credit and can provide additional savings!

Great advice from everyone so far! As someone who works in tax prep, I'd add one more consideration that often gets overlooked - timing your wedding date strategically within December if you do decide to get married this year. Since your tax filing status is determined by December 31st, you could literally get married on December 31st and still file as married for the entire 2024 tax year. This gives you almost the full year to see how your finances actually play out before making the commitment. Also, with a baby due in May 2025, consider that you'll be eligible for the Child and Dependent Care Credit starting in 2025 if you have childcare expenses. This credit can be worth up to $2,100 for one child (20-35% of up to $8,000 in expenses, depending on your income). Combined with the Child Tax Credit of up to $2,000, having a child provides significant tax benefits. One last tip: if you do get married, make sure both of you understand the "kiddie tax" rules won't apply here since we're talking about your own child, but do keep documentation of all baby-related medical expenses throughout 2025 - some may be deductible if they exceed the threshold for medical expense deductions.

As a new single-member LLC owner myself, this discussion has been incredibly valuable! I've been stressing about this exact same issue for weeks. Based on everything shared here, I'm feeling much more confident about my approach. I'm planning to follow the consensus advice: pay from my business account, record as owner draws (not business expenses), and set up that automatic 30% transfer system that several people mentioned. The idea of having a dedicated tax savings account within my business banking sounds like it will eliminate so much of the quarterly payment anxiety I've been having. One thing that really stood out to me was the reminder about self-employment tax being IN ADDITION to regular income tax - I had been calculating wrong and probably would have been short on my payments. The 15.3% SE tax plus whatever income tax bracket you're in really adds up quickly! For other newcomers reading this: the key takeaway seems to be that the IRS doesn't care which account you use, but consistency in your bookkeeping method is crucial. Pick one approach and stick with it. And definitely don't forget to factor in both income tax AND self-employment tax when calculating your quarterly payments. Thanks to everyone who shared their real-world experiences - this is exactly the kind of practical guidance that's hard to find elsewhere!

This has been such a helpful thread for new LLC owners! I'm in my second year of running a single-member LLC and I wish I had found this kind of practical advice when I was starting out. One thing I'd add based on my experience: if you do decide to pay from your business account (which I recommend for the paper trail reasons others mentioned), make sure you're consistent about the timing of recording the owner draw transaction. I learned to record it on the same day I make the payment, not when I initiate the transfer or when it clears. This keeps everything aligned for monthly financial statements. Also, for anyone using QuickBooks - there's actually a specific "Owner's Draw" account type that's separate from regular expense accounts. Using this makes it crystal clear that these payments aren't deductible business expenses, which will save you headaches during tax prep. The 30% automatic transfer strategy really is game-changing. I started doing something similar after my first year and it's eliminated all the stress around quarterly payments. Now I never have to scramble to find the money when deadlines approach!