For business gifts, I'd strongly recommend avoiding cash or personal checks entirely - they're almost impossible to properly document and will likely raise red flags if audited. The IRS wants clear evidence that this was a business expense, not personal spending. A few solid alternatives that work well: - Visa gift cards are actually fine IF you keep excellent records (receipt, business purpose note, proof of delivery) - Branded promotional items that prominently display your logo can potentially qualify as marketing expenses beyond the $25 limit - Gift baskets with a mix of branded and non-branded items (document the branded portion separately) The key is documentation. Whatever you choose, make sure you have: (1) receipt showing purchase, (2) written note explaining the business relationship and purpose, and (3) proof it was actually given to the client. I keep a simple spreadsheet tracking all client gifts with photos of receipts attached. Remember that even if you spend more than $25, you can only deduct $25 per person per year for true gifts. But legitimate promotional/marketing expenses with clear business purpose may qualify for full deduction if properly documented.

Just to add another perspective on this - I've found that timing can be really important with client gifts. If you're giving a gift immediately after landing a new client or receiving a referral, it's much easier to document the clear business purpose. But if you wait months or give gifts randomly without a specific business event, it becomes harder to justify as a legitimate business expense. I typically give gifts within 30 days of a referral or major milestone, and I always include a handwritten note that specifically mentions the business reason (e.g., "Thank you for referring Smith Industries - looking forward to working with them!"). This creates a clear paper trail linking the gift to a specific business purpose. Also worth noting that if you're planning to do this regularly, consider setting up a simple system from the start. I use a basic spreadsheet with columns for date, client name, gift description, amount, business purpose, and receipt location. Makes tax time much easier and shows the IRS you're treating this seriously as a business expense rather than just random personal gifts.

Has anyone used the IRS's Interactive Tax Assistant for this kind of question? I think it has a module specifically about filing status and dependents. Might be worth checking before paying for services.

Just wanted to add another perspective here - I'm a tax preparer and see this situation frequently. The advice about your girlfriend claiming both kids and filing HOH while you file Single is generally correct and usually optimal, but there's one scenario worth considering. If your girlfriend's self-employment income fluctuates significantly year to year, you might want to consider alternating who claims the kids. In years where her business income is very low, she might not have enough earned income to maximize the Earned Income Tax Credit, and you might benefit more from claiming one child for HOH status. Also, since she has self-employment income, make sure she's taking advantage of the home office deduction if she uses part of your home exclusively for her photography business. That can reduce both her income tax and self-employment tax liability. One last thing - document everything about your living arrangements and who pays what expenses. The IRS does occasionally question HOH status and dependent claims for unmarried couples, so having clear records of your household setup will help if any questions arise.

Something I learned the hard way: don't waste money on expensive software right away. Most tax pros use professional software like ProSeries, Drake, or Lacerte, but they cost hundreds or thousands of dollars. Start with the free fillable forms from the IRS website to learn the actual forms and calculations. Then consider TaxAct Professional or TaxSlayer Pro which have lower entry costs. As your client base grows, you can upgrade to the premium options.

As someone who made the transition from retail to tax prep 4 years ago, I want to emphasize that this career change is absolutely doable! The advice here is solid - I'd specifically recommend starting with the IRS AFSP program and then working toward your EA license. One thing I wish someone had told me: tax season is incredibly intense (think 60+ hour weeks from January to April), but the off-season gives you flexibility that retail never did. I now spend summers taking continuing education courses and building my client base. Also consider specializing in a niche as you grow - small business taxes, rental properties, or tax resolution services. The general "do everything" preparers are often competing on price, but specialists can command higher fees. My path was: AFSP certificate → seasonal work at Jackson Hewitt → EA license → now I have my own small practice. The income potential is much better than retail, especially once you build repeat clients who trust you with their finances year after year. Don't let anyone tell you that you need college for this field. Tax law changes constantly anyway, so what matters most is your ability to learn continuously and pay attention to details. Your retail experience dealing with difficult customers will actually serve you well!

Just so everyone knows, not all second look services are created equal. I paid $400 for one last year and they literally just ran my numbers through a different tax software and found nothing. Make sure you ask exactly what their process involves before paying. Ask if they specialize in your industry and what their success rate is for businesses similar to yours. Also ask if they've worked with businesses in your specific state, as state tax opportunities vary widely.

Speaking as someone who handles small business accounting, there's another benefit to second looks that nobody's mentioned yet - they sometimes catch ERRORS that could lead to audits. Last year I had 3 clients get second looks and for one of them, we actually discovered their previous accountant had improperly classified some expenses that could have raised red flags with the IRS. The second look saved them from potential audit headaches, not just money.

Has anyone used the "my529" plan from Utah? I'm in a multi-state situation too (Utah and Idaho) and I've heard Utah's plan has good investment options even for non-residents. Trying to decide if I should put money in both states' plans or just use Utah's for everything.

Great question! I'm dealing with a similar multi-state situation between Florida and Virginia. One thing I learned that might help is to also consider the rollover rules between state plans. If you start with separate 529s in different states and later decide you want to consolidate, most states allow you to roll funds from one 529 to another once per 12-month period without tax consequences. This gives you flexibility to optimize your strategy over time. You could start by maximizing deductions in both states with separate accounts, then potentially consolidate later into whichever plan performs better or has lower fees. Also worth noting - make sure you understand each state's recapture rules. Some states will make you pay back the tax deduction if you roll the money out to another state's plan within a certain timeframe. Virginia, for example, has a recapture period, while other states don't. The administrative overhead of multiple accounts isn't too bad if you set up automatic contributions. I use a spreadsheet to track everything and review annually to see if I want to adjust my strategy.