this post was submitted on 17 Mar 2024
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I always see advice about which software to use and there's always the advice that FreeTaxUSA is the best bang for your buck and does everything you need for when your taxes are "simple." I've used and thought it was great for years. But as my career has grown and no longer filed as a single I've begun to question when my taxes and earnings become "complicated" to the point where it is worthwhile to have a professional do my taxes. Are there general recommended bullet points or scenarios?

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[–] [email protected] 3 points 7 months ago (1 children)

I had no trouble handling my basic W2 and mortgage interest deductions.

Where it got tricky was when I had stock income from RSUs. I found a “professional” who sucked, so I figured out how to do it correctly myself and never looked back.

Also, if you have multiple mortgages due to a refinance, that can get tricky; TurboTax has a nasty bug on this so you might want to pay for an hour of an expert’s time if there’s any new scenario you don’t understand.

[–] [email protected] 2 points 7 months ago (1 children)

What's tricky about RSUs? Doesn't my brokerage account, fidelity in this case, just provide the forms I need to enter? I also thought if I sold the RSU's the second they hit my account there was not really a tax implication since taxes were paid from the gross RSU value so my net RSUs were a lot less than than actual gross grant number of RSU.

[–] [email protected] 4 points 7 months ago

You already paid tax, but also got a 1099, so if you don’t enter the correct cost basis you will be double taxed.