This is such a frustrating situation that so many remote workers are dealing with! I went through the same thing last year when my company suddenly decided that working from home 3 days a week meant I couldn't claim mileage for client visits anymore. What really helped me was putting together a clear timeline showing that my home office arrangement was officially established by my employer, not just something I decided on my own. I included emails where my manager confirmed my hybrid schedule, any home office equipment they provided, and documentation of the regular work I do from home. The IRS is pretty clear that if your employer has established your home as a regular work location (which yours has by officially allowing you to work remotely 3 days a week), then travel from there to temporary work locations like client sites is business mileage, not commuting. The key word is "temporary" - if you're visiting different client sites rather than going to the same location every day, that strengthens your case. I'd suggest creating a simple presentation for your boss showing: 1) Your official remote work arrangement, 2) The varying client locations you visit, 3) The relevant IRS guidance on home-based workplaces. Sometimes employers just need to see it laid out clearly to understand they're interpreting the rules incorrectly.

This thread has been incredibly helpful! I'm dealing with the exact same issue where my employer is claiming that since I work from home, any travel to client sites is considered "commuting" and not reimbursable. One thing I wanted to add that might help others - I found that documenting the *business necessity* of each client visit really strengthened my case. I started keeping a log that included not just the mileage and destination, but also the specific business purpose (client meeting, project site visit, equipment delivery, etc.) and who requested/approved each visit. When I presented this to HR along with the IRS guidance that others have mentioned, it became much harder for them to argue that these were personal commuting expenses. The documentation showed that these weren't routine trips to a fixed workplace, but legitimate business travel to serve different clients at varying locations. I think the key is showing that your situation fits the IRS definition of travel between work locations rather than home-to-office commuting. The more specific you can be about the business nature of each trip, the stronger your case becomes.

This thread has been incredibly helpful for understanding the sports betting tax situation! I'm dealing with something similar - DraftKings winnings that went through multiple payment apps before landing in my bank account. One additional point that might be worth mentioning: if you're in a state where sports betting just became legal recently, make sure to check if there are any state-specific reporting requirements that differ from federal rules. Some states have their own thresholds for tax forms or additional documentation requirements. Also, for anyone reconstructing their records like several people mentioned, don't forget to check your email! Most betting platforms send confirmation emails for deposits, withdrawals, and significant wins. Those emails can help fill in gaps if your platform's transaction history doesn't go back far enough or if you're missing some bank statement details. The timing aspect is crucial too - make sure your gambling log reflects the actual date winnings were credited to your account, not necessarily when you placed the bet. This becomes important when transactions cross tax years or when there are delays between winning and receiving funds. Thanks to everyone who shared their experiences and resources. This is exactly the kind of real-world guidance that's hard to find elsewhere!

This has been an incredibly thorough discussion that really highlights how complex sports betting taxation has become with all these payment apps involved! I'm dealing with a similar situation - ESPN BET withdrawals that went to Venmo, then to my bank account. One thing that hasn't been mentioned yet is the importance of keeping screenshots of your betting platform account summaries, especially the "tax documents" or "annual summary" sections that most platforms have. Even if they don't generate formal tax forms like W-2Gs, many platforms provide unofficial summaries that show total deposits, withdrawals, and net position for the year. I learned this the hard way when trying to reconstruct my records - some platforms only keep detailed transaction histories for 12-18 months, but they often keep annual summaries longer. Taking screenshots now (before platforms purge older data) could save a lot of headaches later. Also, for anyone using multiple sportsbooks, consider keeping a master spreadsheet that consolidates activity across all platforms. This makes it much easier to calculate your overall net gambling income and ensures you don't accidentally double-count transfers between platforms and payment apps. The resources mentioned in this thread (taxr.ai, Claimyr) seem really valuable for people with complex situations. Thanks to everyone for sharing their experiences - this is exactly the kind of practical advice that's impossible to find in generic tax guides!

Did you and your spouse consider whether filing separately is actually saving you money overall? I did this for 3 years because of my wife's student loans, but we finally ran the numbers both ways and realized we were paying about $1,800 more in taxes just to save about $1,200 in student loan payments. Worth double-checking with your actual numbers - sometimes the tax hit from MFS is bigger than the student loan savings!

Great question! I went through this exact same situation last year. The $375k limit applies to each spouse individually when filing MFS, so you're in good shape. Since your mortgage is $560k total and you're splitting it 50/50, each of you would be claiming $280k of mortgage debt, which is well under the individual $375k limit. This means you can each deduct your full portion of the $31,000 interest ($15,500 each). One thing to keep in mind - make sure you're consistent with how you split all home-related expenses (mortgage interest, property taxes, etc.). Also remember that if one spouse itemizes, the other must also itemize, but it sounds like you're both planning to do that anyway. The approach you're taking should work perfectly for your situation!

Slightly off topic but does anyone know if section 179 vehicles have to be over 6000 lbs? Im looking at buying a work vehicle but I'm not sure if my SUV qualifies.

I'd strongly recommend consulting with a tax professional before making any moves here. The recapture rules for Section 179 are pretty strict - when you sell that truck, you'll likely owe ordinary income tax on the sale proceeds up to the amount you originally deducted ($98k). One thing to consider is the timing of both transactions. If you're planning to buy another qualifying vehicle this year, you might want to structure the timing so that the recapture income from the sale is partially offset by the new Section 179 deduction. This won't eliminate the tax hit entirely, but it could help manage the cash flow impact. Also keep in mind that there are annual limits on Section 179 deductions ($1,160,000 for 2023), so make sure you have enough "room" left if you've already taken other business deductions this year. The rules can get complex when you're dealing with multiple transactions in the same tax year.

Just want to add - KEEP GOOD RECORDS of everything! Create a simple spreadsheet tracking: - Exact dates/times you babysit - All payments received - Any expenses related to childcare - Portion of your home used for childcare - Photos of areas used for childcare - Receipts for anything you buy for childcare The IRS loves to audit self-employed people with cash businesses, and childcare is definitely on their radar. Good records are your best defense if you ever get questioned!

Great advice from everyone here! I'm a tax preparer and just wanted to add a few quick clarifications: 1. Yes, you absolutely need to report this income - the $400 threshold for self-employment tax applies to you. 2. For home deductions, you can use either the simplified method ($5 per square foot up to 300 sq ft) or actual expense method. Given that you're only babysitting part-time, the simplified method might be easier. 3. Document everything NOW - create that spreadsheet Oliver mentioned and go back through your Zelle history to reconstruct the dates/amounts. The IRS allows reasonable reconstruction of records. 4. Consider setting aside about 25-30% of future payments for taxes (income tax + self-employment tax). This will help avoid a surprise bill next year. Your sister doesn't need to do anything on her end since this is a personal expense for her, not a business deduction. You're handling this correctly by taking full responsibility for reporting the income yourself!