This thread has been incredibly helpful! I've been making regular Goodwill donations but never really tracked them properly for tax purposes. After reading through all these responses, I realize I need to get more organized about this process. The key takeaways I'm getting are: use the fair market value (not original purchase price), leverage the official donation value guides from Goodwill/Salvation Army, document everything with photos and receipts, and be realistic about item condition. The bunching strategy @Paige mentioned is genius for those of us who are borderline on itemizing. I'm definitely going to start keeping a spreadsheet this year and taking photos before my donation runs. Even if I don't end up itemizing, it's good practice to have the documentation ready. Thanks everyone for sharing your experiences and tips - this community is such a great resource for navigating these tax questions!

One thing I haven't seen mentioned yet is the importance of keeping your donation receipts organized by year. I learned this the hard way when I got audited and had receipts scattered across different files and boxes. Now I keep a dedicated folder for each tax year with all my charitable donation receipts. Also, if you're donating items that might be considered "unusual" or high-value (like artwork, antiques, or collectibles), definitely consider getting a professional appraisal. The IRS is much more likely to scrutinize these types of donations, and having third-party documentation of the value can save you a lot of headaches down the road. For regular household items though, the approach everyone's outlined here is solid - use the charity value guides, be honest about condition, take photos, and keep good records. It's really not as complicated as it seems once you get into a routine!

Has anyone here actually created a retirement account for their kids from S corp earnings? My daughter is 14 and makes about $7k a year in my business and I'm wondering if it's worth setting up a Roth IRA for her or if there's some other tax strategy I should be using.

Great discussion here! I just want to add one thing that's helped me tremendously with S corp payroll for my kids - make sure you're keeping really detailed records of their actual work hours and tasks. The IRS can be pretty strict about "reasonable compensation" even for family members. I created a simple time tracking system where my kids log their hours and what they did each day. For the marketing/photo work, I keep copies of the actual materials they appeared in and notes about which photo shoots they participated in. This documentation has been invaluable when my accountant prepares our quarterly payroll reports. Also, don't forget that you'll need to issue them W-2s at the end of the year just like any other employee. The payroll software I use makes this pretty straightforward, but it's something to plan for if you're doing payroll manually. The Roth IRA suggestion is spot on too - getting them started on retirement savings this early is such a gift you can give them!

Your accountant's caution is completely justified here. Multi-family property sales where you've lived in one unit are among the most complex tax situations in real estate. Beyond what others have mentioned about the 25% primary residence exclusion and depreciation recapture, there are additional complications your accountant is likely considering: 1) **Mixed-use property allocations** - The IRS requires you to allocate expenses, improvements, and depreciation between personal and rental use portions, which can get messy if you've made shared improvements over 7 years. 2) **State tax variations** - Some states don't follow federal capital gains rules and may tax the entire gain at ordinary income rates. 3) **Net Investment Income Tax** - If your income is high enough, you may owe an additional 3.8% tax on the rental portion gains. 4) **Potential audit triggers** - Mixed-use property sales often get IRS scrutiny, so your accountant wants to ensure everything is bulletproof. Rather than asking for a final number, try asking your accountant for a range based on different scenarios (like if you sell for asking price vs. 10% above/below). This gives you planning numbers while acknowledging the variables they can't control yet. The complexity is real, but it's manageable with proper documentation and realistic expectations about the tax liability.

Your accountant is being appropriately cautious, and here's why this situation is genuinely complex beyond just the basic 2-out-of-5 rule: **Primary residence exclusion complexity**: You'll only get the capital gains exclusion on 25% of your gain (the portion you lived in). But calculating that "gain" isn't straightforward when you've been depreciating 75% of the property for years. **Depreciation recapture nightmare**: Every dollar of depreciation you've claimed (or should have claimed) on the rental units over 7 years gets "recaptured" and taxed at 25%. If you haven't been taking depreciation deductions, the IRS still treats it as if you did for recapture purposes. **Section 1250 vs 1202 considerations**: Different parts of your gain may be taxed at different rates depending on how long you've owned it and your income level. **Documentation requirements**: The IRS scrutinizes mixed-use property sales heavily. Your accountant knows that giving you a number now without proper documentation review could leave you exposed later. My suggestion: Ask your accountant to walk you through the calculation methodology and what specific documents they need from you. Then you can at least understand the framework even if the final number has to wait until closing. The "it's complicated" response, while frustrating, is actually protecting you from nasty surprises down the road.

Has your sister checked her contribution statements from when she was working at the previous employer? One possibility is that she accidentally made pre-tax contributions to the 403b for a period of time, then switched to Roth contributions later. If the plan administrator kept everything in one bucket but tracked the tax status separately, that could explain what you're seeing. Another possibility is that there were some employer contributions (like matches) that got lumped into the Roth account but maintained their pre-tax status.

I dealt with this exact same situation when I rolled over my 403b from my previous job at a nonprofit. What you're seeing is likely a combination of a few factors that are more common than you'd think. First, some 403b plans allow what's called "in-plan Roth conversions" where employees can convert pre-tax balances to Roth within the plan. However, the recordkeeping doesn't always cleanly separate these conversions, especially if they happened over multiple years or in partial amounts. Second, your sister may have had periods where she was making both pre-tax and Roth contributions simultaneously, and the plan administrator lumped everything into account buckets that don't perfectly align with tax treatment. The key thing is that Vanguard's system is designed to handle these mixed tax treatments correctly during rollovers. The pre-tax portions will maintain their tax-deferred status regardless of which "bucket" they were sitting in at the old plan. I'd still recommend calling Vanguard after the rollover settles, but in my experience, their rollover team is very knowledgeable about these situations and the automated system usually gets it right. Just make sure to keep all the rollover documentation for your records in case there are any questions down the road.

This is definitely a tricky situation that many small nonprofits face! I've been through something similar and can share a few key insights. First, the tax implications largely depend on your personal use of the vehicle. If it's truly 100% business use, there shouldn't be any taxable benefit. However, if you use it for commuting or personal errands, that portion becomes taxable income that should be reported on your W-2. Your nonprofit will need to use one of the IRS-approved valuation methods (Annual Lease Value, cents-per-mile, or commuting rule) to calculate this. From a liability standpoint, this arrangement does create some risk since you're the legal owner but not the beneficial owner. Make sure you have a comprehensive written agreement that clearly establishes: - The nonprofit's beneficial ownership despite your name being on the title - Specific insurance requirements (they should add you to their commercial policy) - Clear procedures for transferring the vehicle when you leave - Who handles maintenance, registration renewals, etc. I'd also strongly recommend getting an umbrella insurance policy for additional personal liability protection, since you could potentially be held responsible in a serious accident even if the nonprofit's insurance is primary. One practical tip: keep meticulous records of business vs. personal mileage from day one. This will be crucial for proper tax reporting and could protect you in an audit. Many people use apps like MileIQ to make this easier. The arrangement can work well if properly structured, but don't skip the upfront documentation - it's worth paying for an hour with both a tax professional and an attorney to make sure everything is bulletproof!

This is such a common issue with small nonprofits! I went through exactly this situation about 18 months ago with a healthcare nonprofit I work for. The key things that saved me a lot of headaches: **Documentation is everything** - Get a formal written agreement that explicitly states the nonprofit retains beneficial ownership while you hold legal title only for registration purposes. Include specific language about insurance responsibilities, maintenance costs, and the transfer process when you leave. **Tax tracking from day one** - I use Everlance to automatically track my trips and categorize them as business/personal. At year-end, my employer uses the IRS cents-per-mile method to calculate the taxable value of personal use and includes it on my W-2. Much simpler than the Annual Lease Value method for our situation. **Insurance coordination** - This was the trickiest part. We ended up with the nonprofit's commercial policy listing me as a covered driver while also maintaining my personal auto policy with a business use endorsement. Both insurers knew about the arrangement upfront to avoid any coverage disputes. **State considerations** - Don't forget to check your state's title transfer rules! In my state, I had to pay a small transfer fee when we initially put the car in my name, but there's an exemption for transferring it back to the organization later. The arrangement has worked well for us, but having everything properly documented and coordinated upfront was crucial. Worth the time investment to get it right!