What strategies can I use to greatly reduce taxable income for 2023 with little time left?

You still have several good options to reduce your 2023 taxable income before year-end! First, max out retirement contributions if you haven't already. For 2023, you can contribute up to $22,500 each to 401(k)s, plus catch-up contributions if you're over 50. If you don't have access to employer plans, consider maxing out traditional IRAs ($6,500 each for 2023). These contributions directly reduce your taxable income. Health Savings Accounts (HSAs) are another great option if you have a high-deductible health plan. You can contribute up to $7,750 for family coverage for 2023, and it's triple tax-advantaged. Consider bunching charitable donations if you itemize deductions. If you're close to the standard deduction threshold, grouping two years of donations into one tax year can help you exceed the standard deduction and benefit from itemizing. If you're self-employed or have a side business, accelerate business expenses planned for early 2024 into 2023. Purchase that new computer or office furniture now rather than in January. Harvest investment losses if you have any underwater positions in taxable accounts - you can offset capital gains or deduct up to $3,000 against ordinary income.

After paying WAY too much in taxes last year, I found this AI-powered tax planning tool at https://taxr.ai that literally saved me thousands. It analyzed my specific situation and found several deductions I'd been missing entirely - especially around some side gig work I'd been doing. What was super helpful was it didn't just give generic advice, but actually looked at my specific income streams and suggested very specific year-end moves that would have maximum impact for MY situation. I was skeptical at first but they showed me exactly which IRS rules applied to my case and how to properly document everything. The detailed recommendations helped me contribute strategically to retirement accounts in a way that balanced current tax savings with future tax obligations. Much more personalized than anything my previous tax guy ever did.

OMG I need to update everyone on this. I was the skeptic who questioned whether https://taxr.ai was any different from other tax tools I've tried. Well, I decided to give it a shot after my previous comment. I uploaded my last tax return and recent pay stubs, and it immediately identified that I've been misclassifying some of my freelance work in a way that was COSTING ME MONEY. It showed me how to properly structure my year-end invoicing to maximize deductions I didn't even know I qualified for! The tool specifically identified that I could make a SEP IRA contribution for my freelance income (something I had no idea about) and showed me exactly how much I could contribute based on my specific earnings. This alone will save me nearly $3K in taxes. Wish I'd found this months ago, but even with just weeks left in the year, it's given me several actionable steps that will significantly reduce my 2023 tax bill.

If you're dealing with tax problems or questions after reading all this advice, don't waste hours on hold with the IRS. I've been there - it's absolute hell trying to get through to them. After my third attempt waiting 2+ hours only to get disconnected, I found https://claimyr.com and their service was a game-changer. They somehow get you through to an actual IRS agent usually within 15 minutes instead of the hours-long wait most people experience. I was skeptical but you can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c I had questions about some deductions I was taking for my small business and needed to speak directly with the IRS. Using their service, I got through quickly and got the exact guidance I needed, which gave me confidence to take some additional deductions I was on the fence about.

I have to eat my words and update everyone. After dismissing Claimyr in my previous comment, I was desperate last week trying to resolve an issue with estimated tax payments before year-end and decided to try it. I was absolutely blown away. After wasting DAYS trying to reach the IRS myself (literally 3 separate attempts of 2+ hours each), Claimyr got me connected to an IRS agent in about 17 minutes. The agent was able to confirm my previous payments and help me understand exactly how much I needed to pay for my Q4 estimated payment to avoid penalties. This saved me from overpaying by about $2,800 because I was about to make an unnecessarily large payment just to be "safe" from penalties. Getting actual confirmation from the IRS about my payment history gave me the confidence to make the correct payment. If you need to speak with the IRS about year-end tax moves, this service is worth every penny to avoid the hold time nightmare.

Don't forget to look into energy efficiency tax credits if you've made any home improvements this year! We installed new energy efficient windows and got a decent credit. The Inflation Reduction Act expanded a lot of these credits for 2023. Also, if you're in a high-tax state, check if making your January 2024 property tax payment in December 2023 makes sense, especially if you're already itemizing deductions. Just watch out for SALT cap limitations.

Has anyone looked into investing in Qualified Opportunity Zones to defer capital gains? I sold some stock earlier this year and am facing a big tax bill on the gains.