Just wanted to add another approach - I use an HSA that offers a debit card AND a reimbursement option. I intentionally pay for most medical expenses with my cash-back credit card, then submit the receipt for reimbursement through my HSA provider's website. This way I get the cash back rewards on those purchases. Some HSA providers even have mobile apps where you can snap a picture of the receipt and submit it immediately. The reimbursement usually hits my bank account within 3-5 business days. Plus, if you're organized enough, you can actually leave that money in your HSA to grow tax-free and reimburse yourself years later. There's no time limit on when you have to reimburse yourself as long as the HSA was established when you incurred the medical expense!

PSA for anyone using HSAs: The IRS has a complete list of what counts as HSA eligible expenses in Publication 502. Things many people don't realize qualify: chiropractor visits, acupuncture, prescription sunglasses, pregnancy tests, smoking cessation programs, and even mileage driving to medical appointments!

Something everyone's missing here - if you're gambling that much, the casino might have already reported your winnings to the IRS on a W-2G if you hit certain thresholds (like $1,200+ on a slot machine win). If that's the case and you don't file, you're gonna get a nasty letter from the IRS later because they'll know you had that income! Also, make sure your parents know about your gambling income. If it's too high, they might not be able to claim you as a dependent anyway which could mess up their taxes too.

Quick tip from someone who used to work at a casino: keep EVERYTHING for documentation. The IRS loves to audit gambling winnings. Save your player's club statements, ATM receipts from the casino, even parking receipts to prove you were there. Create a log of your gambling sessions with dates and amounts won/lost. If you took cash to gamble with, document when you withdrew it. The more records you have, the better position you'll be in if questioned about your winnings vs losses.

Something nobody's mentioned yet - the IRS audit rate has been dropping for years because of budget cuts. They're mostly focused on high-income earners ($500k+) and blatant red flags now. My accountant told me they're primarily using automated matching systems rather than human auditors for most income levels now. So if your W2s and 1099s match what you report, and your deductions aren't wildly out of line with your profession, you're probably not on their radar.

As someone who's been self-employed for 8 years and has never been audited despite claiming substantial business deductions, I can confirm that the under 1% rate is accurate for your income range. The key thing to understand is that the IRS uses algorithms to identify returns with unusual patterns relative to your industry and income level. Your $85k freelance design income with typical business deductions (home office, equipment, software) is completely normal and unlikely to trigger scrutiny. I've learned that audit anxiety often causes people to under-claim legitimate deductions, which actually costs more money than the minimal audit risk. Document everything properly (I use a simple spreadsheet and photo receipts), keep business and personal expenses separate, and claim what you're entitled to. Your friend's audit was likely triggered by something specific in her return - maybe the home office deduction was calculated incorrectly or she couldn't substantiate it with proper documentation. The IRS doesn't audit people for taking standard business deductions that are reasonable for their profession and income level.

One thing to consider is that your cost basis isn't just the purchase price - it also includes certain closing costs and any capital improvements you've made to the property. So your taxable gain might actually be less than the simple difference between purchase and selling price. For example, if you bought at $780k but paid $15k in eligible closing costs and put another $20k into home improvements, your adjusted basis would be $815k. If you sold for $840k, your actual capital gain would only be $25k, not $60k.

Don't forget to keep detailed records of everything! I went through a similar work-related move after 16 months and the IRS actually audited my return (though it worked out fine in the end). Make sure you have documentation for: your employer's written relocation request or transfer letter, proof of the distance between your old workplace and new workplace (Google Maps screenshots work), records of all home improvements with receipts and before/after photos, and copies of all closing documents from both your purchase and eventual sale. The IRS was particularly interested in proving that the move was truly work-related and not voluntary. Having that paper trail saved me a lot of headaches. Also, if your company is paying for any moving expenses, make sure you understand which parts are taxable vs non-taxable - sometimes the moving expense reimbursements can affect your overall tax situation. Given all the advice here about basis adjustments and partial exclusions, it sounds like you'll likely come out just fine tax-wise, but good documentation will give you peace of mind!

2 Did your settlement include any punitive damages? That part is definitely taxable! My cousin didn't realize this and ended up with a huge tax bill the following year.

Just went through this myself last year after a car accident settlement. The good news is that most of your settlement should indeed be tax-free! The key thing to look for is how your settlement agreement breaks down the payments. In my case, the settlement document clearly stated amounts for medical expenses, pain and suffering, and property damage - all of which were non-taxable. However, there was a small portion listed as "lost income compensation" that I did have to pay taxes on. One thing that caught me off guard was that my lawyer's fees were deducted from the gross settlement amount, but the IRS still considers the full gross amount as the settlement for tax purposes. So make sure you're looking at the right numbers when determining what's taxable vs non-taxable. Also, definitely get a 1099-MISC if your settlement is over $600 - even though most of it won't be taxable, you'll still need it for your records. My advice is to consult with a tax professional just to be 100% sure, especially since you're dealing with a significant amount of money. Better safe than sorry!