Quick tip that helped us: make sure you're calculating the affordability threshold correctly. It's 9.12% of your ENTIRE household income, not just your spouse's employment income. So take your total AGI (including your self-employment income) and multiply by 0.0912 - that's your annual affordability threshold. If the annual cost of adding you to your spouse's plan exceeds that number, you should be eligible for the deduction.

This is a great question that many self-employed individuals face! Based on my understanding of the tax code, your husband should indeed be eligible for the self-employed health insurance deduction. The key is that "affordability" test - if your employer's family plan costs more than 9.12% of your household income, then your husband is not considered to have access to "affordable" employer-sponsored coverage. A few important points to keep in mind: 1. The deduction is limited to your husband's net self-employment income - he can't deduct more than his business actually earned 2. Make sure to keep documentation of your employer's family plan costs in case of an audit 3. This deduction goes on Schedule 1 of Form 1040, not Form 8962 (which is for premium tax credits) The IRS recognizes that just because coverage is "available" doesn't mean it's actually accessible if the cost is prohibitive. Since your family was able to get marketplace coverage based on the unaffordability of your employer's family plan, that's a good indication that the IRS would view your situation the same way for the self-employed health insurance deduction.

Thank you all for this incredibly thorough discussion! As someone who just went through the home buying process six months ago, I wish I had found a thread like this earlier. One additional tip I'd like to share: when you're getting pre-approved for your mortgage, make sure your lender uses realistic tax estimates in their calculations, not just generic percentages. I initially got pre-approved based on a rough 1.2% property tax estimate, but the actual taxes in my target neighborhoods were closer to 2.1%. This significantly affected how much house I could actually afford once I factored in the real monthly costs. Also, regarding the escrow account - don't forget that you'll need to fund it at closing! My lender required 2-3 months of estimated property taxes and insurance to be deposited into escrow at closing, which was an additional $1,800 I hadn't budgeted for. It's not technically a "cost" since it's your money going toward future tax payments, but it's cash you need to have available at closing on top of your down payment and closing costs. For anyone still in the research phase, I'd highly recommend creating a spreadsheet with all the properties you're considering and their actual tax amounts (both current and estimated post-reassessment). It really helped me compare the true monthly costs between different homes and neighborhoods. Good luck to everyone in their home search - it's worth the complexity once you're holding those keys!

This is such a comprehensive thread - I've learned more about property taxes here than in all my other homebuying research combined! I wanted to add one more consideration that hasn't been mentioned: if you're buying in an area with ongoing development or infrastructure projects, your property taxes might increase beyond just reassessment. I discovered this when looking at a house near a planned new school - the special assessment for that project would have added about $150/month to my tax bill for the next 10 years. These special assessments don't always show up in current tax records since they're for future projects, but they're legally binding once approved. Your real estate agent should know about any planned assessments in the area, but it's also worth checking with the local planning department or city council meeting minutes. Also, for those worried about reaching tax offices by phone - many counties now have online chat features on their websites during business hours. I used this to get quick answers about homestead exemption deadlines and it was much faster than calling. The chat representatives could even email me the specific forms I needed. One last tip: if you're working with a buyer's agent, ask them to include a property tax contingency clause in your offer. This gives you a few days after going under contract to review the actual tax documents and back out if there are any surprises like special assessments or higher-than-expected rates. It's a small thing that could save you from a costly mistake!

One thing no one mentioned yet - if you're using the property occasionally for personal use, that complicates things even more. Even a week of personal use can change how expenses need to be allocated. We learned this the hard way when we used our rental for just 10 days ourselves, and it messed up our entire tax calculation.

Your tax preparer's wording was confusing, but they're not technically wrong about the economic effect. The key insight here is that mortgage principal payments aren't deductible expenses, which means more of your rental income remains taxable. Think of it this way: if you collect $2,000 in rent and have a $1,500 mortgage payment ($1,000 principal + $500 interest), you can only deduct the $500 interest portion. So you're effectively paying tax on $1,500 of income instead of $500, making it feel like you're being "taxed on the principal." However, don't forget about depreciation! You can depreciate the building portion of your rental property (not the land) over 27.5 years, which often provides a substantial deduction that helps offset this issue. For a $300,000 rental property where $240,000 is allocated to the building, that's about $8,727 in annual depreciation deductions. Also keep detailed records of all repairs, maintenance, property management fees, insurance, and property taxes - these are all deductible and can significantly reduce your taxable rental income. The principal payments are building equity in your property, which will benefit you when you eventually sell, but they just don't provide current-year tax relief.

Great question about sole proprietorship dissolution! I went through this exact situation last year when I closed my home-based bookkeeping business. One thing that really helped me was keeping detailed records of the original purchase dates and costs of all my business assets. Since you mentioned $15,000 worth of equipment over 3 years, make sure you have documentation showing when each item was placed in service and what depreciation method you used. For your specific situation with the woodworking tools, if you've been depreciating them using MACRS (Modified Accelerated Cost Recovery System), most of your equipment likely falls under the 7-year recovery period. This means items purchased in your first year might be getting close to full depreciation, while newer purchases could trigger recapture if converted to personal use. The delivery van is particularly important to handle correctly since it's listed property. You'll want to calculate what percentage was used for business versus personal use in your final year of operation. If you've been claiming 100% business use but plan to use it for family trips, that conversion needs to be reported properly. I'd recommend creating a spreadsheet listing each asset, its original cost, accumulated depreciation, and current fair market value before making any final decisions. This will help you see which items are already fully depreciated (no tax consequences) versus which ones might create tax liability.

One thing I haven't seen mentioned yet is the impact on your self-employment tax obligations when closing a sole proprietorship. Since you've been filing Schedule C, you've likely been paying self-employment tax on your net business income throughout the years. When you close the business, make sure you understand how this affects your Social Security credits. The self-employment tax you paid on your woodworking business income counts toward your Social Security work history, so you'll want to ensure your final year is properly reported. Also, if you have any outstanding quarterly estimated tax payments scheduled for this year, you'll need to adjust those with the IRS since your self-employment income will drop to zero. You can use Form 2210 to request a waiver of any underpayment penalties if your income changes significantly due to the business closure. Don't forget to keep all your business records for at least 3 years after filing your final Schedule C (or 7 years if you claimed any losses). This includes receipts for all those tools you'll be converting to personal use, in case the IRS has questions about the depreciation calculations later.

Don't forget that there's also Form 8027 (Employer's Annual Information Return of Tip Income) if your business is a "large food or beverage establishment" - basically if you have more than 10 employees. That form has specific tip reporting requirements beyond just the regular payroll forms.

One thing to keep in mind is the timing of when you actually pay out the tips to employees. If you're holding onto credit card tips for a few days before including them in payroll, you need to be careful about the IRS requirement that tips be paid out by the next regular payday after the tip was received. The IRS considers tips to be wages when they're received by the employee, not when you collect them through your credit card system. So if you batch tips weekly with payroll, that's usually fine, but holding them for longer periods could create compliance issues. Also, make sure you're keeping detailed records of daily tip amounts by employee - the IRS may want to see this documentation if they ever audit your payroll tax returns. A simple daily tip log showing date, employee, and tip amount received can save you a lot of headaches down the road.