Does anyone know if TurboTax Premium can help with preparing Form 709? I already pay for the premium version for my rental properties, but I'm not sure if it includes gift tax returns.

I went through this exact situation two years ago when I helped my grandson with his student loans. The separate filing approach you're planning is totally fine - that's exactly what I did. One thing I'd suggest is keeping good records of both filings. I created a simple folder with copies of both my 1040 (after e-filing) and my mailed Form 709, along with all the supporting documentation for the gift. This made it super easy when I had a follow-up question from the IRS months later (nothing scary, just a routine clarification request). Also, don't forget that if your gift exceeds the annual exclusion amount, you're not necessarily paying any tax - you're just using up part of your lifetime exemption. That was the part that confused me the most initially. The Form 709 is more about tracking your lifetime gift totals than actually owing money in most cases. Good luck with your filing! It's really not as complicated as it seems once you get through it the first time.

This is such a common and frustrating issue! I've been buying from European sellers for years and this VAT/tax ID confusion happens all the time, especially with Italian sellers who primarily deal with EU customers. The bottom line is simple: as a US individual making a personal purchase, you absolutely do NOT need to provide any VAT number, tax ID, or codice fiscale. The US doesn't use the European VAT system for consumers. Here's exactly what to tell your seller: "Please enter 'US PRIVATE CONSUMER' or 'EXEMPT - PERSONAL USE' in your shipping system's VAT field. As a United States individual, I don't have a VAT number because the US uses a different tax system. For customs, please complete form CN22 marking this as personal merchandise with the $65 value." You can also explain that exports from Italy to non-EU countries like the US are actually VAT-exempt anyway, so they don't need any tax documentation from you. Your $65 purchase is well under the US de minimis threshold, so no special paperwork is required on our end either. If they're still confused, suggest they contact their local Poste Italiane office - postal workers handle US exports regularly and can guide them through the correct procedures. This is purely a knowledge gap, not a real requirement, and it gets resolved once sellers understand the system differences. Your item will ship!

I've run into this same frustrating situation multiple times when buying from Italian sellers! The issue is that their shipping software often has mandatory VAT/tax ID fields designed for EU business transactions, but as a US consumer, you don't have and don't need a VAT number. Here's what has worked for me every time: Tell your seller to enter "US PRIVATE BUYER" or "N/A - PERSONAL USE" in whatever tax ID field their system requires. Explain that the United States doesn't use the European VAT system for individual consumers - we have a completely different tax structure. For the customs documentation, they just need to complete a CN22 form (since your $65 purchase qualifies for the simpler form) marking it as "merchandise" with the actual purchase value. No tax documentation from you is required for personal imports under $800. You can also mention that exports from Italy to non-EU countries are actually VAT-exempt anyway, so they don't need to collect any tax information from US buyers. If they're still confused, suggest they contact their local Poste Italiane office - postal workers handle US exports regularly and can guide them through the correct procedures. Don't worry about your purchase being cancelled! This is super common and gets resolved once sellers understand they can put something generic in that mandatory field. Most are very cooperative once they realize the system difference between EU business rules and US personal imports.

I've been working in tax prep for about 3 years and wanted to share my perspective on the course options. I actually started with the H&R Block course, which was fine for getting my feet wet, but I quickly realized I needed more comprehensive training to handle complex returns confidently. The game-changer for me was pursuing the EA credential. I used Gleim's study materials and found them excellent - much more thorough than the basic seasonal courses. The EA exam is challenging but worth it - you'll learn about business returns, representation rights, ethics, and advanced individual tax situations that the basic courses barely touch. One thing I wish I'd known earlier: don't just focus on learning tax law. Learn the business side too - client communication, pricing your services, managing deadlines, and staying organized during busy season. Those skills are just as important as knowing the tax code, but most courses don't cover them adequately. If you're serious about making this more than just seasonal income, I'd recommend skipping the basic courses and going straight for EA preparation. It's a bigger investment upfront, but you'll be much better positioned to build a real career in tax preparation rather than just being another seasonal worker making minimum wage.

I've been lurking on this thread and wanted to add my perspective as someone who recently went through this decision process. After reading everyone's experiences, I ended up going the VITA route first and I'm so glad I did. The VITA program really opened my eyes to what tax preparation actually involves day-to-day. You're dealing with real people with real problems - language barriers, missing documents, complicated family situations that don't fit neatly into tax software prompts. The classroom training is thorough but basic, covering individual returns, credits, and deductions. What's invaluable is the supervised practice where experienced volunteers help you work through situations you'd never encounter in a course. I volunteered at a community center and prepared about 150 returns during the season. The variety was incredible - simple W-2 returns, small business Schedule C, rental property, education credits, elderly clients with retirement income. Each return taught me something new, and having mentors right there to answer questions was priceless. Now I'm planning to study for the EA exam this summer, but I feel like I have a solid foundation to build on. Plus, several local tax firms have already reached out to me for next season based on my VITA experience. The hands-on experience and references you get from VITA supervisors seem to carry a lot of weight with employers. If you're on the fence, I'd definitely recommend starting with VITA. It's free, you're helping your community, and you'll get a realistic view of whether tax preparation is something you want to pursue seriously.

Coming from someone who's been in the tax industry for over a decade, I'd strongly recommend going straight for the EA if you're serious about advancing your career. The CRTP might seem like an easier entry point, but it's really limiting your potential right from the start. Here's what I wish someone had told me early on: the EA exam isn't as scary as it seems, especially with your bookkeeping background. You already understand basic accounting principles, which gives you a huge advantage. The three-part structure means you can tackle it piece by piece rather than one massive exam. Given that you're considering a move to Oregon, the EA is a no-brainer. California-specific credentials won't help you there, and you'd essentially be starting over. Plus, even if you stay in California, EA status commands more respect and higher fees than CRTP. My advice? Skip the CRTP entirely, invest in good EA exam prep materials, and dedicate 4-6 months to serious study. The return on investment is so much better long-term. You'll thank yourself later when you're charging $150+ per hour for representation work instead of being stuck at basic prep rates.

As someone who recently went through this exact decision process, I wanted to share my perspective. I ultimately chose the EA route and couldn't be happier with that choice. The key factor for me was scalability. With a CRTP, you're essentially locked into California and limited to basic tax preparation. The EA opens doors not just geographically, but professionally - you can handle complex tax issues, represent clients before the IRS, and command significantly higher fees. Since you mentioned possibly relocating to Oregon, that alone should push you toward the EA. I have colleagues who started with state-specific credentials and later regretted having to essentially restart their certification journey when they moved. From a practical standpoint, the EA exam is challenging but very doable with your bookkeeping background. The three-part structure actually makes it less overwhelming than it initially appears. I used a combination of Gleim for structured learning and supplemented with additional practice questions from other sources. One thing that really helped me was connecting with local EA study groups through the National Association of Enrolled Agents. Having that peer support made a huge difference, especially when tackling the more complex business taxation concepts. Bottom line: if you're serious about advancing in the tax field, go straight for the EA. The time and money investment pays off much faster than taking the incremental CRTP route.

Just FYI as a tax preparer, bring ALL your medical receipts to your appointment, not just COBRA. Many people forget about mileage to medical appointments (17 cents per mile for 2024), prescription costs, dental expenses, eye care, medical equipment, etc. Every dollar helps get you closer to that 7.5% threshold.

Great question about COBRA and taxes! Just wanted to add one important point that might help you save money - if you have any self-employment income from your freelance work, you might qualify for the self-employed health insurance deduction for your COBRA premiums. This is WAY better than the itemized medical expense deduction because it's an above-the-line deduction (meaning it reduces your AGI directly) and you can still take the standard deduction. Since you mentioned having 1099 income, definitely ask your tax preparer about this. The self-employed health insurance deduction lets you deduct health insurance premiums (including COBRA) as long as you have net self-employment income and you're not eligible for coverage through your spouse's employer plan. Given that you're both on COBRA, this could be a huge tax saver. For documentation, bring your 1099s showing the freelance income and all your COBRA payment records. The preparer can determine if this applies to your situation - it could potentially save you way more than trying to meet that 7.5% AGI threshold for itemized medical expenses!