Has anyone else noticed that sometimes the total interest reported on the 1098s doesn't match what you actually paid according to your payment history? My mortgage was sold in August and the sum of both 1098s was about $340 less than what my payment records show for interest.

Great question! I dealt with this exact situation last year when my mortgage was sold in July. You definitely need to add both 1098 forms together - each lender reports the interest they collected during their respective periods of servicing your loan. One thing to watch out for: make sure there's no overlap in the dates. Sometimes there can be a few days where both lenders might report interest, especially around the transfer date. If the numbers seem unusually high when added together, double-check your monthly statements to verify the totals. Also, keep both 1098 forms with your tax records. The IRS receives copies of both forms, so they'll expect to see the combined total reflected in your return. TurboTax should handle this smoothly when you enter both forms separately - it will automatically combine the mortgage interest amounts for your Schedule A.

Quick tip: make sure you're correctly classifying people as contractors vs employees. This is my biggest nightmare as a business owner. If you're telling them WHEN, WHERE and HOW to do the work, the IRS might consider them employees, not contractors. The difference matters ALOT because for employees you need to withhold taxes, pay unemployment insurance, etc. For contractors you just send a 1099. Getting this wrong can result in huge penalties and back taxes!

Great advice from everyone here! I'm actually dealing with a similar situation right now where I have about 6 subcontractors for a large project. One thing I learned the hard way is to get those W-9 forms BEFORE you make any payments, not after. I made the mistake of paying two contractors first and then asking for their W-9s later - one of them completely ghosted me and the other took weeks to respond. Now I'm scrambling to get the paperwork sorted before year-end. Also, keep detailed records of exactly what services each contractor provided and when. The IRS can ask for this documentation if there are any questions about your 1099 filings. I use a simple project tracking spreadsheet that includes dates, amounts, and description of work performed for each contractor. Makes tax time so much easier!

I did doordash last year and messed up my taxes by not tracking my miles properly. KEEP A MILEAGE LOG starting today!! The standard mileage deduction was worth waaaaay more than itemizing all my other expenses. Download a mileage tracking app that records your trips automatically. I use Stride and it saved me over $1800 in taxes last year just from mileage deductions alone.

Hey Paige! I totally get your stress about this - I was in the exact same boat when I started doing gig work alongside my regular job. The good news is that it's really not as complicated as it seems once you understand the basics. Since you have both W-2 and 1099 income, you'll file everything on one tax return but they're handled differently. Your DoorDash income goes on Schedule C (business income/loss), where you can deduct all your legitimate business expenses. Your W-2 income gets reported separately like always. For deductions, you're on the right track thinking about that tablet and hot bags - both are 100% deductible as business expenses since they're specifically for DoorDash. Keep receipts for everything! You can also deduct things like: - Mileage (usually your biggest deduction - track every business mile!) - Portion of phone bill used for business - Car accessories like phone mounts, chargers - Parking fees while delivering - Even a percentage of car washes if you clean your car to maintain professional appearance The key is keeping good records. Start tracking your mileage NOW if you haven't already - that alone will probably save you hundreds in taxes. Don't stress too much, you've got time to get organized before filing season!

I went through this exact same process last year with my SPX options and futures trading! The confusion is totally understandable - TurboTax's interface for 1256 contracts isn't very intuitive. Here's what worked for me: After searching for "Form 6781" and selecting "Yes" for having 1256 contracts, the key is to use the summary amounts from your 1099-B rather than trying to enter individual trades. Your broker should have a specific section for 1256 contracts that shows your total gains/losses. One thing that tripped me up initially was making sure I didn't double-enter these amounts in both the regular capital gains section AND Form 6781. The 1256 contracts should ONLY go in Form 6781, not in the regular stock trading sections. With $14,500 in realized profits, you'll benefit from that 60/40 split (60% long-term, 40% short-term) regardless of how long you held the positions. TurboTax will calculate this automatically once you enter your totals correctly. The "marked to market" question should be "No" unless you've made a special trader election with the IRS, which most retail traders haven't done.

I just went through this exact situation a few months ago when filing my taxes for last year's SPX options trading. The Form 6781 process in TurboTax definitely isn't as straightforward as it should be! One thing that really helped me was double-checking my broker's classification of the trades. I found that my broker had actually missed categorizing a few of my SPX trades as 1256 contracts on the initial 1099-B, but they issued a corrected version later. You might want to verify that all your SPX options and futures are properly marked as Section 1256 contracts on your forms. Also, keep in mind that if you have any wash sale adjustments related to your 1256 contracts, those will need special handling since the wash sale rules work differently for Section 1256 contracts compared to regular securities. The good news is that once you get past the initial confusion, the 60/40 tax treatment actually works out pretty favorably compared to short-term capital gains rates on regular trades. With your $14,500 profit, you'll definitely benefit from having 60% of that treated as long-term gains. If you run into any snags with the TurboTax interface, don't hesitate to reach out - this community has been really helpful for navigating these more complex trading tax situations!

One additional consideration that hasn't been mentioned yet - make sure you understand the timing of when your mom needs to report any capital gains. Even though she may qualify for the $250,000 exclusion on her primary residence, she'll still need to report the sale on her tax return for the year it closes. Since you're managing her finances with the POA, you'll likely be responsible for ensuring this gets reported correctly. The sale should be reported on Schedule D and Form 8949, even if no tax is owed due to the exclusion. Also, if your mom has any cognitive decline that affects her ability to understand financial matters, you might want to consider having a tax professional handle her return for the year of the sale. The documentation requirements and potential complexity of reporting a home sale while managing someone else's finances through a POA can be tricky to navigate solo.

I went through this exact situation with my father's house last year and learned a few hard lessons that might help you. One thing that caught me off guard was the timing of when you need to establish the cost basis - make sure you're collecting all improvement receipts NOW, not after the sale closes. Also, regarding transferring money to your personal account - I'd strongly recommend against doing this directly. Instead, keep the proceeds in an account that's still in your mom's name but that you manage with the POA. This creates a much cleaner paper trail and avoids any potential gift tax complications. If you do need to access the money for her care expenses, transfer smaller amounts as needed with clear documentation of what each transfer is for (medical bills, care facility payments, etc.). This approach protects both of you and makes it much easier if you ever need to account for how the money was used. The tax reporting is also more straightforward when the money stays in her name - you'll just report the sale on her return without having to worry about gift tax implications on your end.