Have u looked into carpooling options? There are apps like Waze Carpool where u might find ppl going to the same area. Might be way cheaper than uber/lyft every day!

Another thing to consider is whether any of your rideshare trips qualify as business travel. If you occasionally travel to client meetings, conferences, or temporary work locations that aren't your regular workplace, those trips could be deductible. Keep detailed records of the business purpose, date, and cost for any trips that might qualify. Also, if you're self-employed or have a side business, trips related to that work (like going to meet clients or pick up supplies) are generally deductible business expenses. Just make sure to keep good documentation and separate business from personal trips. The key is understanding the difference between regular commuting (home to primary workplace) which isn't deductible, versus business travel which can be.

I messed this up last year - had a $25k loss but my tax guy only applied $3k of it. I was so confused but he kept insisting that was the limit. Finally got a second opinion and found out he was completely wrong. Ended up having to file an amended return to properly apply my losses against my gains. Make sure whoever does your taxes understands capital loss carryovers!!

This is such a common area of confusion! I went through something similar when I had significant losses from some tech stock investments that went south. The key thing to remember is that capital loss carryovers work in two stages: first, they offset capital gains with no limit whatsoever. Then, any remaining losses can offset up to $3,000 of ordinary income per year. So in your case with the $27,000 loss carryover and $13,500 gain, you'd use $13,500 of your carryover to completely eliminate the capital gains tax. The remaining $13,500 would then be subject to the $3,000 annual limit against ordinary income - so you'd deduct $3,000 against your regular income in 2025 and carry forward $10,500 to 2026. One tip: make sure to keep detailed records of your carryover amounts and whether they're short-term or long-term losses, as this affects the order in which they're applied against different types of gains. It'll save you headaches down the road!

Lol @ all the complicated answers here. The simple fact is the IRS knows about your gains bcuz your broker reports them. So if you make enough to file a return anyway, just include them. If you don't make enough to file a return, don't worry about it. And FYI - the IRS isnt coming after anyone for a few hundred bucks in unreported gains. They're after the big fish with millions in hidden income, not regular folks with tiny stock sales.

Adding to what others have said - the key thing to remember is that the IRS has automated matching systems. When your broker sends them a 1099-B showing your stock sales, their computers automatically check to see if those transactions appear on your tax return. Even for small amounts like your sub-$1000 gain, if there's a mismatch, you'll likely get a CP2000 notice in the mail asking you to explain the discrepancy. This creates unnecessary paperwork and stress, even if you don't end up owing any additional tax. Since you mentioned these are long-term gains and you're likely in a lower income bracket, you're probably right that they'll be taxed at 0%. But reporting them is still required and honestly pretty straightforward once you have your 1099-B form. Just fill out Schedule D and Form 8949 - it's a few extra lines but saves you potential headaches later. Better to spend 15 minutes reporting them correctly now than dealing with IRS correspondence later!

Has anyone used Drake Tax software for this situation? I'm preparing several S Corp returns with SEP contributions and Drake seems to automatically put the current year's contribution (made in the following year) on Line 17, but I want to make sure it's handling it correctly.

This is such a common source of confusion! I went through the exact same thing when I started handling my family's S Corp taxes. The key insight that finally clicked for me is that SEP contributions are one of the few exceptions to the normal cash-basis timing rules. Think of it this way: the IRS wants to encourage retirement savings, so they created special timing rules that let you make the contribution after year-end but still deduct it for the previous tax year. This gives you time to see your final numbers before deciding on the contribution amount. Just make sure when your brother makes that 2023 SEP contribution in March 2024, he tells the financial institution it's specifically for tax year 2023. They should give you some kind of documentation confirming this designation. Then that amount goes on Line 17 of the 2023 Form 1120S, even though the cash won't leave the business account until 2024. The deadline for making the contribution is the same as the filing deadline for the return (including extensions), so you have plenty of time to get it sorted out.

Has anyone considered prepaid expenses rules? I think there's an exception if you're prepaying for something more than a year in advance. Just wanted to throw that out there in case someone's booking really far ahead.

This is such a helpful thread! I'm in a similar situation as the original poster - I'm a consultant who travels frequently for client meetings and always struggle with the timing of deductions. Based on all the advice here, it sounds like the key is to focus on when you actually paid, not when you used the service. One thing I'd add is to keep really good records of your payment dates, especially if you're using different payment methods (credit cards, bank transfers, etc.). I learned this the hard way when I got audited a few years ago and had to reconstruct my travel expense timeline. The IRS was very focused on the actual payment dates, not the travel dates. For anyone else dealing with this, I'd recommend setting up a simple spreadsheet or using one of the tools mentioned here to track payment dates alongside your travel dates. It makes tax time so much less stressful when you have everything organized properly!