Has anyone done a side-by-side comparison? I'm nervous about missing something if I switch away from TurboTax since they have all my historical data.

I actually did run both TurboTax and FreeTaxUSA side by side the first year I switched, and they came up with identical refund amounts. The only real difference was the interface - TurboTax looks fancier but FreeTaxUSA gets the job done. You can always download your tax return PDFs from previous years and have those for reference. You'll need to manually enter some basic info the first time you use a new service, but after that initial setup, it's smooth sailing. The hundreds of dollars I've saved over the past few years has definitely been worth the small hassle of switching.

This is great advice! I'm in Massachusetts and discovered they have special rules for capital gains on collectibles that are different from federal. Almost missed it until my accountant caught it.

That's actually not a bad idea if they're local! My old job was cool about it. The HR lady even apologized and said a bunch got lost in the mail. Way better than waiting on hold with the IRS.

This is great advice, thank you! I'll start keeping track of my attempts to get it. Do you think a simple log with dates and times of calls would be sufficient, or should I be sending emails so I have written proof?

Email is definitely better because it gives you a clear paper trail. Send a polite email to HR or payroll requesting your W-2, mentioning that you haven't received it yet and the January 31st deadline has passed. If you call, follow up with an email summarizing the call ("As we discussed on the phone today..."). For extra protection, if they don't respond to regular emails after a week, send a certified letter with return receipt. This proves they received your request. The IRS takes this stuff seriously, and if your employer is systematically failing to provide W-2s, your documentation could help with any potential investigation.

Is there a minimum amount for business expenses to be worth tracking? Like, do I need to save receipts for $5 purchases or only bigger things?

There's no minimum threshold - technically even small expenses are deductible if they're legitimate business costs. I personally track everything because those small purchases add up quickly. A $5 expense every workday is over $1,200 annually! I recommend using a receipt-scanning app that links to your accounting software. I snap a pic of every receipt immediately, categorize it, and then I don't have to worry about keeping paper copies. The IRS accepts digital records as long as they contain all the relevant information. Better to track too much than miss deductions!

I went through an audit last year for my LLC. They specifically looked at my home office deduction. As long as you have good documentation (photos of the space, a diagram showing square footage, and records of your total rent/mortgage), you should be fine. Just make sure that space is EXCLUSIVELY for business. That's what they look for.

Thanks for this advice! I hadn't thought about keeping specific documentation of the tax year designation. Will Fidelity automatically generate a receipt showing the 2020 contribution, or should I request something special when I make the contribution?

When you make the contribution online, you'll receive a confirmation that should clearly indicate the tax year. Print this or save a PDF of it. Additionally, I'd recommend taking a screenshot of the contribution page where you select "2020" as the tax year. Fidelity will also generate a Form 5498-SA in May that officially documents your HSA contributions by tax year. This form is sent to both you and the IRS. While you don't need to include it with your tax return, definitely keep it with your tax records. If you want to be extra careful, you can also call Fidelity after making the contribution to confirm it was properly coded for 2020, and make a note of the date, time, and representative's name from that call.

Generally for online transactions, midnight in your time zone on the deadline day is acceptable. However, different HSA providers might have different cutoff times for processing transactions, especially if they require manual verification or processing. To be safe, I'd recommend making the contribution at least 2-3 business days before the deadline. I made this mistake last year trying to fund my HSA on April 15th at 9pm, and while my provider (not Fidelity) accepted it, they initially coded it for the wrong tax year and it was a hassle to get fixed.

5 These are great suggestions. I didn't think about maxing out retirement accounts! I haven't contributed much to my 401k this year so I could definitely increase that. How would I know if I have any investments at a loss that I could sell? Would I just look at my current portfolio and check what's down from my purchase price?

14 Yes, exactly! Just look at your current portfolio and identify any investments that are currently valued lower than what you paid for them. Those are your potential tax-loss harvesting opportunities. Your brokerage should show your cost basis and current value for each position. Remember that if you sell something at a loss and buy the same or a "substantially identical" security within 30 days before or after the sale, that's considered a wash sale and you can't claim the tax loss. You can buy something similar but not identical to maintain market exposure while still harvesting the tax loss.

9 I talked to my Fidelity advisor about almost this exact same situation last year. They basically confirmed what everyone here is saying - you're stuck with the tax bill for the year the gains were realized, but they did help me put together a tax-loss harvesting strategy for the following year to minimize the ongoing impact. Depending on your broker, they might offer free consultations that could be helpful.