I switched from TurboTax to FreeTaxUSA three years ago and have been super happy. My taxes include a W-2, some dividends, and mortgage interest - nothing too fancy. FreeTaxUSA handled everything just fine and saved me like $70 compared to what TurboTax wanted to charge. The interface isn't quite as polished but it gets the job done. One thing to watch out for with TurboTax is how they try to upsell you throughout the process. You start thinking you're getting the $39 version and somehow end up paying $89+ by the end because of "necessary" upgrades. FreeTaxUSA is much more straightforward with pricing.

Has anyone tried Credit Karma Tax (now Cash App Taxes)? It's completely free for both federal and state, which seems too good to be true compared to the $100+ I paid for TurboTax last year.

I went through bankruptcy with about $500k in IRS debt last year. Few things to keep in mind: 1) Make sure you file all required returns before bankruptcy. Any unfiled returns will definitely not be dischargeable. 2) Be careful about any transfers of assets in the years leading up to bankruptcy - the court looks back several years and can claw back anything they consider inappropriate. 3) Document EVERYTHING about your current financial situation very thoroughly. The courts are more skeptical when large tax debts are involved. 4) The IRS will scrutinize your case much more closely than a typical bankruptcy. They may send their own attorneys to challenge the discharge of tax debt. 5) Your trading accounts and history will be examined closely. Be prepared to explain any large withdrawals. Good luck! It's a stressful process but there is light at the end of the tunnel.

Don't overlook the emotional toll this will take. Bankruptcy with the IRS involved is WAY more stressful than regular bankruptcy. I went thru this in 2022 and spent almost every night unable to sleep. Get some support - therapist, support group, whatever. The stress can be unbearable especially when ur young and feel like ur life is ruined. Also prepare for after bankruptcy. Trading might be harder without capital. Have a backup plan for income. The discharge feels amazing but then reality hits that you need to rebuild completely.

Something nobody's mentioned yet - make sure your mom doesn't claim herself as independent on her own tax return if she files one for her part-time job. You'll both get flagged if she claims herself and you also claim her as a dependent.

One other thing I learned when claiming my parent - if your mom has medical expenses that you pay, you can include those when you itemize deductions on your return. Helped me get above the standard deduction threshold last year and saved some money.

Have you tried looking into tax attorneys who offer consultation services? I had a similar situation last year when I was starting a small business but wanted to handle the ongoing tax work myself. I found a tax attorney who charged me for a 2-hour consultation where I brought all my questions. She answered everything, gave me some resources to reference, and didn't try to sell me on recurring services. It wasn't cheap (about $400 for the session), but the advice saved me probably thousands in potential mistakes.

Don't overlook the free resources! I know you said you're willing to pay, but I've had great experiences with VITA (Volunteer Income Tax Assistance) volunteers. If your income is under $60k, they offer free tax help. Even if you don't qualify for their free filing help, many of the volunteers are really knowledgeable and can answer questions. The same goes for Tax-Aide from AARP - they focus on seniors but often help others too.

As a manager, this is actually concerning from a financial literacy standpoint. My company started offering basic financial wellness sessions because we found similar misconceptions were common. Your employee isn't alone - a survey from a few years ago found that about 40% of Americans didn't understand that tax refunds are returns of their own money. Many see it as a "bonus" and plan major purchases around it. Maybe suggest some basic financial literacy resources rather than just being frustrated? Part of leadership is helping team members grow, and this could be a growth opportunity.

Sadly, I've found that a lot of people look forward to tax season specifically for this "bonus" and build it into their annual financial planning. My sister literally plans her family vacation around her tax refund every year, and gets angry when I try to explain she could have that money throughout the year instead. Some people actually use overwithholding as a forced savings method because they know they wouldn't save the money if it came in smaller amounts in their regular paychecks. In a weird way, it makes sense psychologically, even though financially it's giving an interest-free loan to the government.