Quick question - how does this work for someone who has two teaching jobs? I teach at two different districts (one main job, one evening adult ed) and I'm worried they're not withholding enough from either job. Should I adjust my W-4s?

With two teaching jobs, you're right to be concerned. Each employer's payroll system only "knows" about the income they're paying you, not your total income from all sources. So both systems are calculating withholding as if that's your only income, which almost always results in underwithholding. You should definitely complete a new W-4 for both positions. On Step 2 of the W-4, check box (c) for multiple jobs, or use the worksheet to calculate a more precise additional withholding amount. You might also want to specify an additional dollar amount to withhold on line 4(c) to make up for the potential shortfall.

OMG YES. My district's payroll department is a disaster. I got a promotion last year and they somehow lost my W-4 in the process. Went 3 months with them withholding as if I was single with zero dependents (I'm married with 2 kids). My checks were tiny and it took forever to fix!

I switched to FreeTaxUSA after having similar problems with TurboTax. WAY better for rental properties and it handles Schedule E much more intuitively. Plus it's cheaper.

That's not accurate - reinvesting profits doesn't make the income tax-free. You still need to report all income from your rental. The renovations and furniture aren't fully deductible in the year you buy them either - they need to be depreciated over several years (typically 5-7 years for furniture and 27.5 years for home improvements). You can deduct normal operating expenses like cleaning, utilities, and supplies in full for the current year, but capital improvements have to be depreciated according to IRS schedules. You're still taxed on your net income even if you're using that money to improve the property.

Thanks for that info - I hadn't heard about the moratorium! Do you know if that affects claims that have already been submitted or just new ones going forward?

The moratorium primarily affects new claims submitted after September 14, 2023. Claims already in the system before that date should continue to be processed, though possibly with additional scrutiny. The IRS has also stated they're prioritizing processing the backlog of previously submitted claims, so in some ways, if you already have a claim in the system, this might actually be good news as they focus resources on clearing existing claims before accepting new ones. If you haven't submitted yet, I'd recommend getting your documentation very thoroughly organized before filing.

What software did you use? I'm considering doing this myself but worried about making mistakes like this.

Thank you! That's super helpful about being specific with the description. Would "Professional Photography and Videography Services" be too long for that field? And for Part IV vehicle expenses - I've been tracking my mileage to photo shoots. Is there a minimum amount of business miles before it's worth claiming?

Professional Photography and Videography" Services is a perfect description -'it s clear and specific without being too long. The character limit gives you plenty of room for that.'There s no minimum threshold for claiming mileage expenses - if'you ve legitimately used your vehicle for business purposes, you can claim those miles. Even small amounts add up to deductions that save you money. Just make sure you have a mileage log with dates, destinations, purpose, and miles driven. The standard mileage rate for 2024 is 67 cents per mile, so those trips to photo shoots could add up to a significantdeduction.

But be careful with home office deduction. I heard it's a big audit trigger. Is it really worth the risk?

Did you try negotiating at all? I'm wondering if there's any flexibility with their prices or if it's just take it or leave it once they tell you the final amount.

I actually did try to negotiate this year! When they told me the price jumped to $389, I mentioned I was considering trying a cheaper option like TaxSlayer. The manager came over and offered me a "returning customer discount" that brought it down to $329. So there is some flexibility, but you have to speak up. The other thing I've learned is that prices can vary between different H&R Block locations, even in the same city. The office in the wealthier part of town charges more than the one in the shopping center near me. Might be worth calling a few different locations for quotes.

I used TurboTax this year for a somewhat complex return (W2, 1099-B with stock sales, rental property). Their premier version was about $119 plus $49 for state filing. BUT they charged me an extra $59 for the Schedule E for rental property and another $39 for "expert review" of my stock sales. So I ended up paying around $270 all in. Still cheaper than H&R Block quoted me ($499), but not as cheap as their advertisements suggest. Their interface is pretty good though, walks you through everything step by step. Just be aware of the add-on fees.