I've been sending tax payments by mail for over a decade and certified mail is definitely the way to go for amounts over $1,000. A few years ago, I had a regular mail payment get "lost" for nearly a month - turns out it was sitting in a pile somewhere at the processing center. The IRS was actually pretty understanding once I provided my certified mail receipt, but it was still weeks of stress I didn't need. For your $4,000 payment, the certified mail fee is absolutely worth it. Just make sure you keep that receipt in a safe place with your tax documents - you'll want it for at least 3 years in case any questions come up later. Also, if you're really worried about timing, you can drop it off directly at your local post office counter rather than using a mailbox. They'll postmark it right in front of you so there's no question about the date.

As someone who's dealt with the IRS for years, I can't stress enough how important certified mail is for tax payments over $1,000. The stories here about payments getting delayed or "lost" are unfortunately all too common during peak filing season. The IRS processes millions of checks in March and April, and while most make it through fine, you really don't want to be the exception. For your $4,000 payment, that certified mail fee is essentially insurance against weeks of stress and potential penalties. I always tell people to think of it this way - would you mail $4,000 cash to anyone without tracking? Same principle applies here. The peace of mind alone is worth every penny of that fee, and you'll sleep much better knowing you have proof of delivery.

Quick tax tip - if your total non-cash donations for the year exceed $500, you MUST file Form 8283 with your return. I learned this the hard way and got a letter from the IRS about my kitchen donation.

Great advice from everyone here! Just wanted to add that you should also keep detailed records of your donation process. I recommend taking timestamped photos of the items before donation, getting measurements, and noting any defects or wear patterns. When I donated my kitchen items last year, I created a simple spreadsheet with each item, its condition, measurements, and my estimated value with notes on how I determined that value (comparable sales, age, condition factors, etc.). This documentation was invaluable when preparing my taxes. Also, don't forget to factor in installation costs when researching comparable values - cabinets that are easy to remove and reinstall are worth more than custom built-ins that would require modification. Since yours are being picked up by Habitat, they're likely standard sizes which helps maintain their value. One last tip: if your total donation value approaches $5,000, consider getting a professional appraisal. It costs money upfront but can save you major headaches if the IRS questions your valuation later.

This is a really complex situation that touches on several different tax and financial planning considerations. Based on what you've shared, here are the key points to consider: **Roth IRA Withdrawal Rules:** - You can withdraw your original contributions (the money you put in) at any time without taxes or penalties - However, withdrawing earnings for private K-12 tuition would trigger a 10% penalty plus income taxes - You'd need to track your contribution basis carefully to avoid touching earnings **Alternative Options to Consider:** - 529 plans (as mentioned) can now be used for K-12 private tuition up to $10,000 per year per child - Coverdell ESAs have always allowed K-12 expenses but have low contribution limits - Home equity loans or education loans might preserve your retirement savings **Hidden Gotchas:** - FAFSA impact: Even tax-free Roth withdrawals count as "untaxed income" on financial aid forms, potentially reducing college aid eligibility - Opportunity cost: Money withdrawn now loses years of tax-free growth potential Given that you're 43 and have twins, I'd strongly recommend getting a comprehensive analysis before making any moves. The tools mentioned earlier in this thread (like taxr.ai) could help you model different scenarios and their long-term impacts. You might also want to speak with a fee-only financial planner who can look at your complete financial picture. The fact that you're thinking about this carefully shows you're on the right track - just make sure you understand all the implications before deciding!

Great question about balancing education funding with retirement planning! As someone who works in tax preparation, I see this dilemma frequently with parents of private school students. A few additional considerations that haven't been mentioned yet: **State Tax Implications:** Depending on your state, there might be additional benefits or penalties to consider. Some states offer tax deductions for 529 contributions but not for education expenses paid from other sources. **Timing Strategy:** If you do decide to use some Roth contributions, consider spreading the withdrawals across multiple tax years rather than taking a large lump sum. This can help minimize the FAFSA impact since it's based on prior-prior year income. **Documentation is Critical:** Make sure you have clear records of your contribution history. The IRS doesn't track this for you - it's your responsibility to prove what portion of your Roth IRA consists of contributions versus earnings. Services like the ones mentioned earlier can help, but maintaining your own records is essential. **Consider a Phased Approach:** Maybe use a small portion of Roth contributions for year one while exploring other funding sources (parent PLUS loans, scholarships, work-study programs) for subsequent years. The $30K annual cost for both kids is substantial - that's $120K over four years. Before tapping retirement funds, also consider whether the private school experience is worth potentially compromising your financial security later in life. Sometimes the "cheaper" option of public school plus tutoring or enrichment programs can achieve similar outcomes. Would love to hear what approach you ultimately decide on!

One approach that worked well for my cousin and me was setting up an escrow account specifically for property taxes and other shared expenses. We each contribute our 50% share monthly (so about $283 each per month for your $6,800 annual tax bill). The account automatically pays the tax bill when due, and we both have access to statements showing exactly what each person contributed. This removes the stress of one person having to front the entire tax payment and wait for reimbursement. It also creates a clear paper trail for tax purposes since each person's contributions are documented. Most banks can set this up as a simple joint account with automatic transfers from your individual accounts. Just make sure the account agreement specifies that each person owns their contributions, not 50% of the total balance. The key is getting this arrangement documented in your co-ownership agreement so both the monthly contributions and the purpose of the account are legally clear. This way if your brother's income becomes unpredictable, you're not scrambling to cover his portion at tax time.

I'd recommend getting a formal partition agreement drafted by a real estate attorney. This is different from just a co-ownership agreement because it specifically addresses what happens if the co-ownership relationship breaks down. In your partition agreement, you can include the 50/50 tax responsibility, but also cover scenarios like what happens if your brother stops paying his share for multiple years. The partition agreement can establish that if one owner defaults on tax payments, the other owner can pay the full amount and then has the legal right to either: 1) Place a lien on the defaulting owner's share of the property, or 2) Force a sale of the property to recover the unpaid amounts. This gives you real legal recourse beyond just having a piece of paper saying he owes 50%. Michigan law is pretty favorable for this type of arrangement, and having it properly recorded with the county clerk gives you maximum protection. The upfront cost of getting this done right (probably $500-800 for a good attorney) is way less than what you could lose if things go sideways with your brother's finances down the road.

You can actually generate Form 1098 without expensive software! The IRS provides free fillable forms on their website that you can complete and print. Just go to irs.gov and search for "Form 1098 fillable." You'll need to manually enter the borrower's information, SSN, the total interest they paid you, and your information as the lender. If you want something more automated, there are also inexpensive online services like TaxAct or FreeTaxUSA that can generate 1098s for under $20. Much cheaper than QuickBooks if you're only doing one seller-financed property. Just make sure you keep good records throughout the year - track each payment showing principal vs interest breakdown. I created a simple spreadsheet with columns for payment date, total payment, principal portion, and interest portion. Makes filling out the 1098 much easier at year-end!

Great comprehensive advice everyone! As someone who's been through this maze multiple times with different seller-financed properties, I'd add one more crucial point that often gets overlooked - make sure you're charging at least the Applicable Federal Rate (AFR) for interest, or the IRS may impute additional interest income to you. The IRS publishes AFR rates monthly, and if your interest rate is below the AFR for the month you made the loan, they can treat the difference as additional taxable income to you AND as a gift to the buyer (which could trigger gift tax issues if it's significant). I learned this the hard way on my first seller-financed deal where I was being "generous" with a below-market rate. My CPA caught it during review and we had to amend some filings. Now I always check the AFR before setting terms - you can find the current rates in IRS Revenue Rulings or on their website under "Applicable Federal Rates." This is especially important for family transactions or situations where you might be tempted to offer a really low rate to help the buyer qualify. The tax implications can end up costing both parties more than just charging a market rate from the start.