Great question! I've been using FreeTaxUSA's professional version for preparing returns for family and friends. It's much more affordable than the big names - around $25 per federal return plus state fees, and you can manage multiple clients under one account. What I really like about it is that it handles all the common situations you mentioned (W-2s, standard deductions, basic credits) really well, and the interface is clean and straightforward. You're not paying for a bunch of bells and whistles you probably won't need for simple returns. One thing to keep in mind - make sure you're comfortable with the responsibility aspect. Even with "basic" returns, there can be tricky situations that pop up (like unreported income, dependents with SSN issues, etc.). Having a good relationship with your clients about what you can and can't handle is key. I always tell people upfront that if their situation gets complicated, I'll refer them to a CPA. Also seconding what others said about the PTIN - definitely get that sorted first. It's free and required by law if you're charging for prep services.

Something I wish someone had mentioned to me when I started - keep really good records of what you charge each client and any expenses related to your tax prep business. Since you're earning income from this (even if it's just $35-65 per return), you'll need to report it on your own taxes. I'd suggest setting up a simple spreadsheet to track client payments, software costs, PTIN fees, any supplies you buy, etc. This becomes business income and you can deduct legitimate business expenses. Just makes everything cleaner come tax time for yourself. Also, consider asking clients to pay you via check or electronic transfer rather than cash so you have a clear paper trail. Makes record-keeping much easier and looks more professional too.

Great question, Derek! I went through this exact same confusion with my RSUs from Microsoft last year. Based on what you're describing with Fidelity automatically selling shares to cover taxes, you're definitely dealing with a "forced sale" situation rather than net settlement. Here's what you need to know: Your company should already be reporting the full fair market value of all 130 RSUs as ordinary income on your W-2 for the year they vested. This covers the tax on the compensation aspect. However, you'll also need to report the sale of those 26 shares that were sold for tax withholding on Schedule D. The tricky part is that your 1099-B from Fidelity might show an incorrect cost basis (often $0) for those sold shares, which would make it look like you have a big capital gain when you actually don't. Since you already paid ordinary income tax on the full value through your W-2, the cost basis for those sold shares should equal the fair market value on the vesting date. If the 1099-B basis is wrong, you'll need to use Form 8949 to make the adjustment. Most people miss this and end up paying tax twice on the same income. The remaining 104 shares you keep have a cost basis equal to their FMV on vesting date, so when you eventually sell those, any gain/loss is calculated from that point. Hope this helps clarify things!

Derek, you're dealing with a really common source of confusion that trips up a lot of people with RSUs! Based on your description of Fidelity using sell-to-cover and only 104 shares ending up in your account while 26 were sold, this is definitely a "forced sale" scenario. The good news is that your employer has likely already handled most of the heavy lifting by including the full value of all 130 RSUs as ordinary income on your W-2 when they vested. This means you've already paid income tax on the compensation value of those shares. However, you do need to report the sale of those 26 shares that were sold to cover taxes on Schedule D. Here's the catch that gets most people: your 1099-B from Fidelity probably shows a $0 cost basis for those sold shares, which would create an artificial capital gain. Since you already paid ordinary income tax on their full value, the correct cost basis should be the fair market value on the vesting date. You'll need to use Form 8949 to make this basis adjustment - otherwise you'll end up paying tax twice on the same income. The 104 shares you kept don't need to be reported until you actually sell them, and their cost basis will be the FMV on the vesting date. This is one of those areas where the tax code creates unnecessary complexity, but once you understand the pattern it becomes much clearer!

This whole situation really highlights how the tax code can create unexpected hardships for seniors, and I feel for your aunt dealing with this confusing situation. The 85% Social Security taxation she's experiencing with Married Filing Separately status is unfortunately correct based on current IRS rules. What's particularly frustrating about her case is how those 21 days of living together in December triggered the harsh MFS treatment for the entire tax year. The IRS rule is very black and white - ANY cohabitation during the tax year means up to 85% of Social Security benefits can be taxable with virtually any other income when filing separately. For some context on why this happens: when you're married filing separately and lived with your spouse during the year, the threshold for Social Security taxation drops to essentially $0. This means her $22,100 in work income immediately pushes her into the 85% taxation category, with no 50% middle ground available. Looking ahead to next year, your aunt and her husband really should consider the financial benefits of filing jointly. With their combined situation - her Social Security income and his non-Social Security income - they might stay under the $44,000 threshold where only 50% of Social Security becomes taxable instead of 85%. The potential tax savings could be substantial. I'd recommend they sit down with a tax professional who can run the actual numbers comparing MFS vs MFJ for their specific situation. Sometimes seeing the real dollar difference helps reluctant spouses understand why cooperation on tax filing benefits both parties financially.

I'm really sorry your aunt is dealing with this frustrating tax situation. As a newcomer to understanding these complex Social Security taxation rules, I've learned so much from reading through everyone's explanations here. What strikes me most about your aunt's case is how those 21 days in December essentially created a year-long financial penalty that she probably never saw coming when she got married. The idea that ANY cohabitation during the tax year triggers the harsh MFS treatment seems incredibly unfair, especially for seniors on fixed incomes who are just trying to find companionship later in life. From everything I've read here, it sounds like the 85% taxation rate she's experiencing is unfortunately correct under current IRS rules, but there's definitely hope for better outcomes next year if she and her husband can work together on joint filing. Given that he's younger and not collecting Social Security yet, their combined income situation might actually work in their favor for avoiding the higher taxation brackets. I'd really encourage your aunt to share some of these responses with her husband - sometimes seeing multiple explanations of how much money they could potentially save by filing jointly helps reluctant spouses understand why cooperation benefits everyone. The tax code shouldn't force people to choose between personal happiness and financial security, but at least understanding these rules can help minimize the impact. This thread has been incredibly educational about how marriage timing can have such dramatic tax consequences. Thank you for sharing your aunt's situation - it's helping many of us learn about these important but often overlooked tax implications.

This has been such an incredibly valuable discussion! As someone new to this community who's been struggling with a similar HSA/FSA transition question, I can't express how helpful all of your shared experiences have been. I'm in almost the exact same situation with my company's April-March benefit year. I've been contributing to an HSA through March 2024, but I'm planning to switch to a PPO plan with FSA options starting April 1st. Reading through this thread has completely clarified the month-by-month eligibility approach - I can contribute to my HSA through March, then cleanly transition to FSA contributions starting in April. The practical tips shared here go so far beyond just understanding the basic rules. Things like: - Getting written confirmation from plan administrators about transition timing - Setting up spreadsheet tracking for expenses from different accounts - Planning 2-3 months ahead for FSA contribution estimates - Checking payroll system lead times for stopping/starting deductions - Keeping digital records of all receipts and communications I'm especially grateful for the IRS Publication 969 reference and the interactive tax assistant tool mentions. Having official resources to double-check the month-by-month calculations gives me so much more confidence. One question for the group - has anyone dealt with HSA provider fees changing when you stop regular contributions? I'm wondering if my HSA account will start charging maintenance fees once I'm no longer making monthly contributions, and whether that affects the long-term strategy of keeping those funds for future qualified expenses. Thanks again to everyone for creating such a comprehensive resource. This thread should honestly be stickied as a guide for anyone dealing with non-calendar benefit years and HSA/FSA transitions!

This thread has been absolutely incredible! As a new community member who's been wrestling with a similar HSA-to-FSA transition, I can't thank everyone enough for sharing such detailed, practical advice. I'm dealing with our company's September-August benefit year, and I was completely confused about whether I could max out my HSA through August 2024 and then switch to an FSA starting September 1st. The month-by-month eligibility rule that everyone has explained makes perfect sense now - as long as there's no overlap in the same month, I can absolutely make this transition work. What really stands out to me is how much more valuable this community discussion has been compared to trying to get answers from official sources. The combination of technical rule explanations (like the IRS Publication 969 reference) with real-world implementation advice (payroll lead times, fee structures, record-keeping strategies) covers everything someone in this situation actually needs to know. I'm definitely going to follow the advice about: - Creating a comprehensive summary document with IRS citations for my benefits team - Setting up digital tracking for receipts and reimbursements from different accounts - Getting written confirmation about transition timing from both HSA and FSA administrators - Being conservative with my first-year FSA contribution estimate while I learn my spending patterns The strategic timing advice about planning medical expenses based on which account provides the best advantage is brilliant too - I never would have thought to actively coordinate things like annual eye exams or dental cleanings with my FSA plan year. Thanks for creating such an amazing resource! This thread really should be the go-to guide for anyone navigating these complex benefit transitions.

This thread has been incredibly valuable! As someone who's been wrestling with the same solo 401(k) reporting confusion, seeing all these real-world experiences and the consistent guidance about Schedule 1, Line 16 for sole proprietors is exactly what I needed. What really helped me was the explanation about thinking of yourself as both employee AND employer as a sole proprietor - that's why both contribution types flow to your personal return rather than being split between business and personal deductions. It finally makes the logic clear! For those still setting up their plans, I'd add one small tip: when you're comparing providers, also check their customer service quality for tax-related questions. I went with Schwab and their support team has been really helpful when I had questions about contribution timing and limits mid-year. Wesley, your numbers look right based on everything discussed here. That $34,506 total on Schedule 1, Line 16 is the way to go. The peace of mind from having this community confirm the approach is worth its weight in gold! Thanks to everyone who shared their expertise - this is exactly why I love this community for navigating the complexities of self-employment taxes.

This has been such an enlightening discussion! As a fellow solo business owner who's been dragging my feet on setting up a solo 401(k) because of the tax reporting confusion, this thread has been a game-changer. The consistent guidance about Schedule 1, Line 16 for sole proprietors really cuts through all the conflicting information out there. I've been going back and forth between different sources for months, but seeing multiple experienced folks (including a tax preparer!) confirm the same approach gives me the confidence I needed. Wesley, your situation mirrors mine almost exactly - similar income levels and the same confusion about where everything gets reported. Seeing your numbers worked out and confirmed by the community is incredibly helpful for visualizing how this actually works in practice. I particularly appreciate how this discussion went beyond just "what" to do and explained "why" it works that way. Understanding that as sole proprietors we're both employee and employer makes the Schedule 1 reporting logic finally click. Plus all the practical implementation tips about automatic contributions and record keeping - those are the details that make the difference between theory and successful execution. Thanks to everyone who shared their real-world experiences. This is exactly the kind of peer support that makes navigating self-employment so much more manageable!