One option nobody has mentioned yet is that many credit unions and community organizations offer free tax prep through VITA (Volunteer Income Tax Assistance) programs. The income limit for these is typically higher than the Free File programs - often around $60k for individuals or $120k for joint filers. Check with your local credit union, library, or community center. The volunteers are IRS-certified and it's completely free.

Has anyone tried Cash App Taxes? I heard they offer completely free federal AND state filing with no income limits. I'm nervous about using something linked to a payment app though.

Another thing you might want to consider is forming an S-Corp instead of operating as a partnership. I switched last year and it's saving me thousands in self-employment taxes. With an S-Corp, you pay yourself a "reasonable salary" which is subject to FICA taxes (like self-employment tax), but then you can take the rest as distributions which aren't subject to self-employment taxes. You still pay income tax on all of it, but avoiding SE tax on part of your business income is huge. There are some additional costs with an S-Corp (more complex tax filing, possible state fees, etc) but at $24k in business income you're right on the edge where it might start making sense.

I was in almost the exact same situation! Made $58k at my job and about $25k from my consulting business. Owed almost $8k total in federal taxes. One thing I discovered - make sure your tax preparer is deducting all legitimate business expenses. I switched to a CPA who specializes in small businesses and she found nearly $5k in deductions my previous preparer missed. Things like part of my internet bill, cell phone, home office, some travel costs, etc. Also, are you making quarterly estimated tax payments? That won't reduce your total tax bill, but it helps spread it out so you don't get hit with one huge bill (and possibly underpayment penalties).

Another option is to check if your investment app integrates directly with tax software. I use one of the major tax prep programs, and it can automatically import all my trading activity directly from several brokerages. Saves tons of time and reduces the chance of errors.

Dont forget that if your trades were all done on the same platform, you might be able to use the composite method for reporting. Basically instead of listing each trade, you can group them by category (short-term vs long-term) and just report the totals. Check box 3 on Form 8949 if you're going this route.

There are legitimate ways to legally not have to file taxes if your income is below certain thresholds. For 2025, if you're single and under 65, you don't need to file if your income is below $14,350. Different thresholds apply for other filing statuses.

I work for a state tax agency (not the IRS) and I can tell you that "under the radar" is basically a myth these days. Between W-2s, 1099s, mortgage info, and banking data, the government has a pretty comprehensive picture of your financial situation whether you file or not. Not filing just means giving up control of your tax situation and potentially leaving money on the table.

Don't forget about Required Minimum Distributions! Since you mentioned only withdrawing from Roth accounts now, I'm assuming you might have traditional IRAs or 401ks too? Once you hit 73, you HAVE to start taking RMDs from those accounts, which could push more of your Social Security into taxable territory in future years. Might be worth considering some Roth conversions now if you're in a lower tax bracket.

Just a heads-up on PA taxes - while PA doesn't tax Social Security, they DO tax distributions from IRAs, 401ks and other retirement accounts (except military). Even if you paid PA tax on the money when you contributed, they tax it again when you withdraw. One of the few states that does this. Roth withdrawals are the exception since they're federally tax-free. So your strategy of using Roth money is smart from a PA perspective too!