Great question about mileage tracking! As someone who's dealt with similar situations, I wanted to add a few key points that might help clarify things for you and your brother. For your pet sitting business, since you work from your apartment for both your main job and run your pet care business from there, your home definitely qualifies as your principal place of business. This means you can deduct mileage from your apartment to each client's home - these are legitimate business trips to temporary work locations. For your brother's OT visits, the situation is a bit more nuanced. If he goes directly from his medical center job to client homes, he can deduct the full mileage from the medical center to the client location. The key is that he's traveling between two work locations for business purposes. However, if he goes home first and then to clients, he can only deduct from his home to the client. One thing I'd strongly recommend is starting a detailed mileage log RIGHT NOW if you haven't already. Include date, starting point, destination, business purpose, and actual miles driven. The IRS is pretty strict about contemporaneous records, so apps like MileIQ or even a simple notebook in your car can save you major headaches later. Also keep in mind that the standard mileage rate for 2024 is 67 cents per mile, which adds up quickly when you're doing a lot of business driving!

This is such a timely question! I just went through something similar with my freelance graphic design work. One thing I learned that might help both of you is the concept of "regular work location" vs "temporary work location." For your pet sitting business, since each client's home is typically a temporary work location (you're not there regularly for more than a year), the mileage from your home office to each client is fully deductible. Just make sure you're actually using your apartment as your business headquarters - doing admin work, storing supplies, etc. Your brother's situation is actually pretty advantageous! When he travels directly from his regular job (the medical center) to his OT clients, that entire trip counts as business mileage because he's going between work locations. The IRS doesn't consider this commuting - it's legitimate business travel. One tip that saved me during tax season: start using the voice memo function on your phone to quickly log trips while you're driving. I just say "Tuesday, March 5th, home to Johnson residence on Oak Street for dog walking, 4.2 miles" and then transfer it to my mileage log later. Much easier than trying to remember everything at the end of the week! Also, don't forget you can choose between the standard mileage rate (67 cents for 2024) or actual expense method, but you have to pick one and stick with it for that vehicle.

I adjunct at a community college too! For my $500ish biweekly checks, I have them withhold $100 for federal taxes. My spouse and I are in the 22% bracket with our combined incomes, and this has worked out almost perfectly for the past two years. You could try a similar percentage. Just remember that teaching income stacks on top of your other income for tax bracket purposes, so it's getting taxed at your highest marginal rate. Don't make the mistake I made the first year where I only had 10% withheld because I thought that's what the bracket would be if it was my only job!

I'm dealing with a similar situation with my part-time consulting work! One thing that really helped me was using the IRS Tax Withholding Estimator on their website. You can input all your income sources - your full-time job, your spouse's income, and your teaching income - and it will give you a pretty accurate recommendation for additional withholding. Since you're married filing jointly with two full-time incomes plus the teaching gig, you're likely in the 22% or 24% bracket. For your ~$435 biweekly checks, I'd probably start with requesting around $85-95 in federal withholding. You can always adjust it later if needed by submitting a new W-4. The key thing to remember is that this side income is being taxed at your marginal rate since it's "on top of" all your other income. Better to err on the side of slightly overwithholding than getting hit with underpayment penalties!

I'm a CPA and want to offer another perspective. While good tax preparers can often find additional deductions, a $10K difference sounds concerning. Here are some possibilities for such a large difference: 1. The preparer might be taking aggressive positions that could trigger an audit 2. They might be claiming credits you're not eligible for 3. They could be incorrectly classifying personal expenses as business expenses 4. They might have found legitimate deductions you missed in previous years and filed amendments Ask for a detailed explanation of what's creating the difference. If they can't explain it clearly or seem evasive, that's a huge red flag.

Has anyone compared getting their taxes done at one of those storefront places (like H&R Block or Liberty Tax) vs those software programs vs an independent CPA? I'm wondering if there's really that much difference between all three options.

Don't forget to look into a SEP IRA or Solo 401k as alternatives. As self-employed individuals, you can contribute much more pre-tax money to these accounts than to a traditional 401k at an employer. While this doesn't directly help with 529 contributions, reducing your overall tax burden may free up more money that you can then put toward 529s with after-tax dollars.

Something nobody's mentioned yet - if you're really committed to funding those 529s, look into Coverdell ESAs as another option. They're more limited ($2k per year per beneficiary), but they cover K-12 expenses too, not just college. My accountant recommended using both types of accounts for our kids.

I just dealt with this last year! I started a photography business, spent about $1200 on equipment and a website, but only made $200 in actual revenue. My tax guy said I could absolutely deduct all those expenses against my other income. The key thing he told me was to show a "profit motive" - basically that I'm trying to make money, not just pursuing a hobby. He had me create a simple business plan, keep logs of time spent working on the business, and document all my marketing efforts. I filed a Schedule C showing a loss for the first year and had no issues. Don't forget you can also deduct home office expenses if you have a dedicated space for the business, even pre-launch!

Great question! I went through something similar when I started my consulting business. Based on my experience and what I learned from my CPA, you should definitely be able to deduct those $650 in startup costs. The IRS considers you "in business" when you're actively working toward launching with genuine profit intent - which it sounds like you clearly have. Your website development, inventory purchases, and business cards all demonstrate legitimate business activity, even without sales yet. A few tips that helped me: - Keep a detailed log of all business-related activities (even time spent researching suppliers, working on your website, etc.) - Save all communications with vendors, web developers, etc. as proof of active business pursuit - Consider getting an EIN if you haven't already - it helps establish business legitimacy - Document your business plan and marketing strategy, even if informal When you file, you'll likely use Schedule C and can claim up to $5,000 in startup costs for your first year. The remaining expenses can be amortized over 15 years. Since you're clearly working toward launch (not just daydreaming), you should be fine claiming these as legitimate business expenses. Just make sure to keep excellent records in case the IRS ever asks questions. Good luck with your launch!