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Have you considered making an extra payment to your student loans if you have any? Interest on student loans is deductible up to $2,500 depending on your income, though with your household income you might be phased out of this deduction. Also, if either of you is self-employed or has any 1099 income, you could make business purchases you were planning for early 2024. New computer, office equipment, professional subscriptions, etc.
We don't have any student loans left fortunately, but my wife does have some consulting income on top of her regular job. That's a great idea about accelerating some business purchases - she was planning to upgrade her home office setup in January anyway. Is there a minimum amount of 1099 income needed to make this worthwhile?
There's no minimum threshold for 1099 income to take business deductions. As long as your wife's consulting work is a legitimate business activity (not just a hobby), she can deduct ordinary and necessary business expenses against that income. Since she was already planning the office upgrade, accelerating it into 2023 makes perfect sense. Just make sure the purchases are actually made and put into service before December 31st - ordering isn't enough, you need to receive and start using the items this year. Keep excellent records of the purchases and how they relate to her consulting work.
Has anyone mentioned charitable donations yet? With your income level, this could be a significant tax saver. If you normally give to charity, consider bunching multiple years of donations into 2023. You could also look into a donor-advised fund - you get the full tax deduction this year but can distribute the money to charities over future years.
Donor-advised funds are amazing for tax planning! We did this last year and it worked great. You can even donate appreciated stock directly to the fund and avoid capital gains taxes completely while still getting the full deduction.
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You should check if both W-2s are using the correct filing status and withholding allowances. Sometimes when you switch payroll systems, your W-4 information doesn't transfer correctly. I had this same issue last year when my company switched from ADP to Paychex. Make sure both payroll processors have the same W-4 information. Also, if you have any other income (investments, side gigs, etc.) that could be pushing you into a higher bracket too.
That's a good point, I hadn't thought about that! When we switched payroll systems, I don't think I filled out a new W-4 for the second one - they might have just used default withholding which would explain the issue. Do you think it's worth asking my HR department if I can see what withholding settings they had for me on both systems?
Absolutely ask your HR department! They should be able to tell you exactly what withholding instructions they had on file for each system. Default withholding typically assumes you're single with no dependents and only one job, which often results in underwithholding if that's not your situation. I'd recommend getting copies of both W-4s they have on file, then filling out a new one with the correct multiple job calculations. The IRS has a good tax withholding estimator on their website that can help you get it exactly right for your situation.
Has anyone else noticed that payroll systems are TERRIBLE at calculating withholding when you have multiple jobs or income sources? This is like the 3rd post I've seen about this same issue. The whole system seems designed to make people mess up and owe money.
It's not really that payroll systems are terrible - they're doing exactly what they're designed to do. The problem is they only know about the income they're processing. It's actually on us to tell our employers to withhold extra when we have multiple income sources.
That makes sense, but it still feels like the system is unnecessarily complicated. Like why can't the IRS just figure out how much I should be paying based on what I made last year and tell my employers? Seems like they deliberately make it confusing so people mess up and they collect penalties.
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Has anyone tried TaxSlayer? I hear it's cheaper than TurboTax but not sure if it's any better interface-wise.
TaxSlayer is ok but I found it confusing for itemized deductions. Kept getting different numbers than I expected and couldn't figure out why.
Thanks for the info! I'll probably try FreeTaxUSA based on all the recommendations here. The dated interface doesn't bother me as much as TurboTax's constant upselling. I appreciate the heads-up about the itemized deduction issues. I don't itemize anymore with the higher standard deduction, so hopefully that won't be a problem for me.
I switched to H&R Block Online last year from TurboTax and found it much more straightforward! It lets you jump directly to forms and has less upselling. Might be worth checking out too.
How much did you end up paying for H&R Block compared to TurboTax? And did you find it easier to navigate? My main frustration is just wanting to directly enter my forms without going through their "life changes" questionnaire every time.
I paid about $70 for H&R Block's Deluxe version compared to $120 I was paying for TurboTax. It was definitely easier to navigate - they have a "forms mode" that lets you go directly to specific forms without going through all the interview questions first. You can still use the interview mode if you want guidance, but it's completely optional. The interface feels less cluttered too, and I didn't get constant popups trying to upgrade me to more expensive versions.
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I'm a retail trader who does about 500-1000 trades per year, and I've never paid per-transaction fees. That's absolutely ridiculous. I use FreeTaxUSA and just import my CSV files from my brokers. Total cost? $15 for the software. Even if you don't want to DIY, most CPAs I've talked to charge a flat $100-200 additional fee for Schedule D reporting, regardless of transaction count. Your preparer is trying to make a killing off you because they think you don't know better. For 2020 specifically, those COVID credits are pretty valuable, so definitely file, but find someone charging a reasonable rate!
Did you have to do anything special with FreeTaxUSA for options trades specifically? I've heard they're treated differently than regular stock transactions for tax purposes and want to make sure I'm doing it right.
For options in FreeTaxUSA, you just need to make sure your import file correctly identifies them as options contracts with the right expiration dates and strike prices. The software handles the different tax treatment automatically. One thing to watch for is that some brokers (especially Robinhood back in 2020) sometimes didn't properly classify certain spreads or multi-leg option strategies in their export files. If you did any complex options strategies, you might need to double-check those specific entries, but for simple buys and sells it works perfectly without any special steps.
Dealt with this exact issue for my 2020 filing. I found a middle ground by asking my CPA to just charge me their hourly rate instead of per transaction. Ended up paying around $400 total for a return with 300+ trades since I had everything organized from my brokers already. Maybe ask your preparer if they'd consider an hourly rate alternative? If they refuse, that's a red flag that they're just trying to milk you for cash.
This is the way. I'm a bookkeeper (not tax professional) and NO reasonable preparer should be charging per transaction when software can import these in bulk. Either hourly or a reasonable flat fee is standard practice for high-volume traders.
Diego Fisher
Another tax benefit angle to consider for your investor clients - if they have properties that have been sitting on the market for a while before staging, make sure they know they can potentially deduct carrying costs during that period (mortgage interest, property taxes, utilities, etc.) as ordinary expenses rather than adding them to basis. Adding professional staging services often shortens time on market, which can actually increase their effective ROI by reducing these carrying costs. My tax advisor pointed this out last year, and when I did the math, I realized that staging actually "paid for itself" in tax benefits from reduced carrying costs, even before considering the higher sale price. Make sure your clients are tracking these time periods carefully!
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Henrietta Beasley
•This is interesting - does this apply even if the property is unoccupied during renovation? I have a couple properties that sit empty for 2-3 months during renovations before I stage them and list them. Can I deduct those carrying costs as ordinary expenses too?
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Diego Fisher
•Yes, it absolutely applies during renovation periods too! The key distinction is whether the property is "held for sale" or "held for production of income" during that time. During active renovation periods for a flip property, the property is considered to be in preparation for sale, so those carrying costs (mortgage interest, property taxes, utilities, insurance, etc.) can generally be deducted as ordinary expenses rather than being capitalized into the basis. This is especially true if you're considered a "dealer" for tax purposes rather than just an investor.
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Lincoln Ramiro
Something nobody's mentioned yet is the timing of when you stage the property can affect the tax treatment. If staging is done as part of the initial renovation/prep work, some tax pros will advise capitalizing it as part of your basis. But if it's done after the property is otherwise ready for sale, it's more clearly a selling expense. I actually changed my business practice based on this - I now complete ALL renovation work first, take dated photos of the completed unstaged property, THEN bring in staging as a separate distinct marketing phase. This creates a clearer paper trail showing staging as a selling expense rather than a capital improvement.
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Faith Kingston
•That's a really smart approach! Do you have any issues with the IRS questioning this distinction? I'm worried about having my staging expenses disallowed if audited.
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Lincoln Ramiro
•I've been doing this for 6 years now and haven't had any issues with the IRS. The key is documentation and consistency. I keep a clear project timeline for each property that shows when renovation was completed and when staging began. I also make sure my staging invoices are separate from any contractor or renovation invoices, with clear dates. It's also important to have a consistent business practice. I don't try to treat similar expenses differently on different properties. I've developed a written business policy that explains my approach to staging as a marketing expense, which would help demonstrate my intent if ever questioned during an audit.
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