One tip that saved me tons of money: check if your local university library has access to tax resources. I use my alumni status to access Bloomberg Tax and other premium databases for FREE. You can often get a community member library card even if you're not an alum. Those databases would cost thousands otherwise. Worth checking out!

This is such a valuable discussion! As someone who's been preparing taxes for about 5 years, I'd add that "The Complete Book of Small Business Legal Forms" by Sitarz has been incredibly helpful when working with small business clients. It helps you understand the legal structures behind different entity types, which makes the tax implications much clearer. For staying current with tax law changes, I also recommend following the AICPA Tax Section newsletters and joining local tax preparer groups on LinkedIn. The peer discussions there often provide practical insights you won't find in textbooks. One thing I wish I'd known earlier - don't just focus on technical knowledge. Client communication skills are equally important as your practice grows. "The Trusted Advisor" by Maister helped me transition from being just a preparer to being a true advisor to my clients.

Watch out about the health insurance thing! If he files independently and isn't claimed as a dependent, he might not be eligible to stay on mom's health insurance plan until 26. Some insurance companies have different rules about this. My daughter got kicked off my plan when she filed independently at 22 even tho the ACA says coverage til 26.

Just wanted to add something that might help with your decision - even if your son technically qualifies as your dependent based on the support test, you should definitely run the numbers both ways before deciding. Since he's working and paying tuition himself, he might qualify for the American Opportunity Tax Credit if he files independently, which can be worth up to $2,500. If your income is too high, you might be phased out of education credits anyway. Also, if he's low income, he could potentially qualify for the Earned Income Tax Credit filing on his own. The support test calculation can be tricky - don't forget to include the health insurance his mom pays ($1,440/year) as support provided BY the parents, not by him. And yes, you need to calculate fair market rental value for his room. Look at similar room rentals in your area. I'd suggest using a tax calculator to compare both scenarios - you claiming him vs. him filing independently - and see which gives your family the better overall tax outcome. Sometimes the student gets more benefit from filing alone than the parent saves from claiming them as a dependent.

I went through a similar partnership disposal situation last year and can confirm that "Complete disposition" is the right choice for your brewery sale. Since you received a lump sum and completely transferred your ownership interest, that's exactly what complete disposition means. One thing to watch out for - make sure you're properly accounting for your share of any partnership liabilities you were relieved of as part of the sale. This gets added to your amount realized for calculating gain/loss, even though you didn't receive it as cash. Also, if the brewery had any depreciated assets, inventory, or unrealized receivables, part of your gain might need to be reported as ordinary income rather than capital gains. The key is getting your adjusted basis calculation right. You'll need your original investment plus your cumulative share of partnership income, minus any distributions you received over the years, plus/minus other basis adjustments. If your K-1s over the years didn't clearly track this, you might need to reconstruct it from your records or contact the partnership's accountant.

Based on your description, "Complete disposition" is definitely the correct choice since you sold your entire 15% interest and received a lump sum payment. You're no longer a partner in the brewery, which is exactly what complete disposition means. A few important things to double-check for your tax filing: 1. **Debt relief**: As others mentioned, if you were relieved of your share of any partnership liabilities (loans, accounts payable, etc.), that amount needs to be added to your sale proceeds when calculating gain/loss, even though you didn't receive it as cash. 2. **Basis calculation**: Make sure you have your adjusted basis correct - this includes your original investment, plus your share of partnership income over the years, minus any distributions you received, plus/minus other basis adjustments from your annual K-1s. 3. **Hot assets**: Since it's a brewery, check if there's any inventory, accounts receivable, or depreciated equipment that could trigger ordinary income treatment on part of your gain rather than capital gains treatment. Your final K-1 should have helped with some of this information, but brewery partnerships don't always provide complete disposition details. If you're missing critical information for the gain calculation, definitely reach out to the partnership's accountant before filing. The good news is that selecting "Complete disposition" in TurboTax will prompt you through the necessary forms (Schedule D, possibly Form 8949) to properly report the sale.

Don't forget that the self-employed health insurance deduction is an adjustment to income (above-the-line) rather than an itemized deduction or business expense. You don't actually claim it on Schedule C! It goes on Schedule 1, Line 17.

Great discussion here! I went through this exact transition two years ago and can confirm that ACA marketplace plans definitely qualify for the self-employed health insurance deduction. The key thing that helped me was understanding that COBRA isn't considered "employer-subsidized" since you're paying 102% of the premium cost. One practical tip: if you're starting self-employment mid-year like I did, make sure to keep detailed records of when your self-employment actually began versus when you left your corporate job. There might be a gap between leaving your job and officially starting your consulting business, and you can only deduct premiums for the months you were actually self-employed. Also worth noting - if you're expecting variable income in your first year of freelancing, consider whether you might qualify for Premium Tax Credits on the marketplace. Even if you don't think you'll qualify based on your corporate salary, your actual self-employment income might be lower than expected, especially in year one when you're building your client base. The math usually works out better with an ACA plan + the self-employed deduction versus COBRA, but definitely run the numbers for your specific situation!

Tbh most of my clients just send me the blank W9 form when they ask for it. Makes it easier for everyone. Not everyone knows where to find the form or which version to use. If u want it done fast just attach the PDF in your email.

From an administrative perspective, you're not required to provide the blank W9 form, but it's often the most practical approach. I work in government contracting and we always include the current W9 form with our initial request - it eliminates confusion about which version to use and removes any barriers for the contractor. The key thing to remember is that you need this information for your 1099-NEC filing, and the contractor is legally obligated to provide it when you've paid them $600 or more. I'd recommend sending one polite email with the blank form attached and a clear deadline: "Please complete and return the attached W9 form by [date] so I can properly report your payment for tax year 2024." If they still refuse after that, document the refusal and proceed with backup withholding as others have mentioned. Most contractors will comply once they understand it's a legal requirement, not just a favor you're asking.