I actually took Jackson Hewitt's classes two years ago and had a very similar situation - wanted to learn business tax prep but was concerned about the time and money investment. Here's what I discovered: The free training really is quite basic - mostly focused on individual returns, basic credits, and how to navigate their software. Business taxation gets maybe 2-3 hours total, and it's very surface level. However, I did find value in the client interaction experience and learning how tax software works in general. What I ended up doing was taking the JH classes, working one season there (made about $1,600 total), and then using that experience to get into a local CPA firm the following year. The firm was impressed that I could handle difficult clients and work efficiently under pressure - skills I definitely developed at JH. For actually learning business taxation, I supplemented with community college courses during the off-season. That combination worked well - the practical client experience from JH plus the deeper tax knowledge from formal education. The community college course covered Schedule C, depreciation, business expense categories, and other small business tax issues in much more detail than JH ever could. My advice: if money is tight and you need to start earning something right away, JH can be a stepping stone. But plan to invest in additional education if you're serious about business tax preparation. The AFSP program that others mentioned is also excellent and free.

I've been researching this exact question for weeks and this thread has been incredibly helpful! Based on everyone's experiences, it's clear that Jackson Hewitt's free classes are really just an introduction to basic tax prep, not the comprehensive business tax education I'm looking for. The hybrid approach that keeps coming up makes a lot of sense - using JH for practical client experience while getting real business tax education elsewhere. I'm particularly intrigued by the IRS Annual Filing Season Program that several people mentioned as a better foundation. One thing I'm wondering about is the timing of making this transition to more serious tax work. For those who started at JH and moved to better opportunities - did you find it was worth staying multiple seasons to build more experience, or was one season sufficient to demonstrate competency to better employers? I'm trying to balance gaining enough experience to be marketable while not getting stuck in a low-paying situation longer than necessary. Also curious about networking opportunities - did working at JH help you make connections in the local tax prep community, or were you pretty isolated within their system? I'm wondering if there are better ways to start building professional relationships in this field. The reality check about pay has been sobering but helpful. It sounds like treating this as an educational investment rather than expecting significant income is the right mindset, at least initially.

As someone who works in disability advocacy, I wanted to add another important perspective to this amazing discussion. The ADA angle that Yara mentioned is absolutely crucial and could be a game-changer for your cousin's friend. Under the ADA, employers have an obligation to provide reasonable accommodations that ensure equal access to employment benefits. In this case, the twins' shared work situation isn't by choice - it's a direct result of their disability. Splitting W-2 reporting or providing detailed documentation to ensure both twins receive proper Social Security credits could very well be considered a reasonable accommodation that the employer is legally required to provide. I'd suggest framing any conversation with HR/payroll not just as a request for help, but as a discussion about ADA compliance. This gives them much stronger legal standing and could make the employer more receptive to making the necessary changes to their payroll systems. Additionally, they might want to reach out to disability rights organizations who may have dealt with similar employment issues for conjoined twins. While rare, there are advocacy groups that specialize in unique disability-related workplace challenges and might have valuable precedents or resources. This situation really highlights how important it is to consider disability rights alongside tax and financial planning. The intersection of all these areas shows why getting comprehensive professional guidance is so valuable.

This has been one of the most fascinating and comprehensive discussions I've ever seen on this subreddit! As a newcomer to the community, I'm absolutely amazed by the collective expertise and genuine care everyone has shown for such a unique situation. What started as a straightforward tax question has evolved into an incredibly thorough analysis covering tax law, Social Security implications, ADA compliance, retirement planning, state tax considerations, and disability advocacy. The progression from immediate practical solutions to long-term strategic planning has been remarkable to follow. I'm particularly struck by how the discussion has revealed both challenges and unexpected opportunities - like the potential for doubled retirement contributions and other per-person benefits that most people don't have access to. It's a great reminder that unusual circumstances, while complex, can sometimes offer unique advantages when handled properly. The consensus that's emerged seems solid: file separate returns this year with detailed explanations, work proactively with the employer on future W-2 handling using ADA compliance as leverage, get official IRS guidance documented, and think holistically about the long-term financial implications. The emphasis on thorough documentation and establishing consistent precedents is particularly wise. Your cousin's friend is incredibly fortunate to have someone advocating for them and seeking out this level of comprehensive advice. This thread should honestly be preserved as a resource - there can't be many places where such rare circumstances have been analyzed with this depth of expertise and care. Thank you all for creating such an educational discussion!

One thing I'd add to all the great advice here - don't overthink this! I went through a similar situation when I received two large checks from a business sale. I was worried about "looking suspicious" but honestly, the banks barely blinked. I ended up doing exactly what you're considering - one check to my regular bank for immediate expenses, and one directly to my investment account. Both transactions went smoothly with no questions asked. The only "issue" was a 3-day hold on the larger check at my investment firm, but that's standard policy for them on any deposit over a certain amount. The key thing that gave me peace of mind was keeping all my paperwork organized (sale agreements, etc.) even though nobody ever asked for it. Having legitimate sources for the money means you really don't need to worry about how you split the deposits. Your plan sounds perfectly reasonable - go with whatever is most convenient for your financial management!

I've been through a very similar situation recently and wanted to share what I learned. I had three large checks from a business sale that I needed to deposit - two over $15k and one around $8k. After researching extensively (and honestly overthinking it way too much initially), here's what I discovered: 1. **Your plan is perfectly fine** - Splitting the deposits between your checking and brokerage accounts is actually smart financial management, not suspicious activity. 2. **Documentation is key** - Since you mentioned inheritance and property sale, make sure you have copies of the estate documents, closing statements, or whatever paperwork shows the legitimate source. You probably won't need them, but having them organized gives peace of mind. 3. **The "flagging" concern** - Banks file reports based on patterns and suspicious behavior, not just dollar amounts. Two legitimate check deposits from documented sources won't raise red flags, especially when you can show clear paper trails. 4. **ACH transfers between your own accounts** - These are completely normal and won't trigger any special reporting. The money is already in the banking system once you deposit the checks. My advice: Go with your original plan. Deposit one check in checking for expenses and one directly into your brokerage account. It's the most efficient approach and there's absolutely nothing suspicious about managing your money this way. The whole experience taught me that legitimate transactions with proper documentation rarely cause issues, regardless of the amounts involved.

Has anyone actually filed a BOI report yet? I'm trying to prepare for mine (Jan 2025 deadline) and wondering how complicated the actual process is. Do I need to gather a bunch of documents first?

I went through this exact same confusion with my single-member LLC! Here's what I learned after consulting with a CPA and doing a ton of research: Being the sole member of an LLC doesn't make you a "sole proprietor" in the legal sense - you're still operating an LLC entity. However, for tax purposes, the IRS does treat single-member LLCs as "disregarded entities" (similar to sole proprietorships) by default. For BOI reporting, what matters isn't your tax classification but whether you meet the specific exemption criteria. The most common exemption is for "small operating companies" which requires: - Under 20 full-time equivalent employees - Under $5 million in gross receipts/revenue from US sources - Physical office within the United States Since you mentioned it's just you running things with no employees, you likely meet the first two criteria. The key question is whether you have a physical US business address (not just a PO box or virtual office). My advice: Don't assume you're exempt just because you're the only person involved. Check all the exemption criteria carefully, and when in doubt, it's better to file than risk penalties. The actual filing process is pretty straightforward once you determine you need to do it. Hope this helps clarify things for you!

I'm dealing with this exact same issue right now! Got my 1099-R yesterday and it's showing the full distribution amount in box 1 with code 4D, but boxes 2a and 5 are completely blank. I've been contributing to this nonqualified annuity for about 6 years and know I shouldn't owe taxes on all of it. Reading through everyone's responses here has been super helpful. I think I'm going to try contacting the insurance company first to see if they'll issue a corrected form, but if that takes too long I'll calculate my own cost basis from my records. I've kept all my statements showing contributions over the years, so I should be able to figure out exactly how much I put in versus earnings. Thanks for posting this question - it's reassuring to know I'm not the only one dealing with this frustrating situation!

This is such a common and frustrating issue with nonqualified annuities! I dealt with something very similar last year and can offer some perspective from someone who's been through the whole process. First, you're absolutely correct that you shouldn't pay taxes on your principal - only on the earnings portion. The insurance company definitely dropped the ball by not filling in boxes 2a and 5 properly. Box 5 should show your total investment (cost basis) and box 2a should show only the taxable earnings portion. Here's what I'd recommend based on my experience: Start by gathering all your annuity statements and contribution records to calculate your total cost basis. Then contact the insurance company and firmly request a corrected 1099-R - don't take "no" for an answer initially. However, don't let their timeline dictate your filing deadline. If they can't get you a corrected form quickly enough, you can absolutely file using your own calculated cost basis. Most tax software will allow you to override the 1099-R when you indicate that the taxable amount wasn't calculated correctly. Just make sure to keep excellent documentation showing how you arrived at your cost basis calculation. I ended up having to file with my own calculations because my insurance company took forever, and I had no issues with the IRS. The key is having solid records to back up your numbers if ever questioned.