How could I optimize my tax strategy for better returns?

Thanks for the info! Quick question - if I do the home office deduction, does that increase my chances of getting audited? I've always heard that's a red flag. Also, for the quarterly payments, how do you even figure out how much to pay?

The home office deduction isn't the audit trigger it once was, especially if you're reasonable and honest about it. Just make sure the space is exclusively used for work - a dedicated room or partitioned area works best. Don't claim your kitchen table where you also eat dinner. For quarterly payments, you need to estimate your annual tax liability and divide by four. You can use last year's income as a starting point and adjust based on your expected earnings. The IRS Form 1040-ES has worksheets to help calculate this. Payments are due April 15, June 15, September 15, and January 15 of the following year.

Does it actually connect with the IRS or does it just give recommendations? Like, can it file for you or is it more of an advisor?

I'm kinda skeptical of these AI tax tools. How does it compare to just going to a human tax professional? Is it really catching all the deductions a pro would find?

It doesn't connect directly with the IRS or file for you - it's more of a comprehensive analysis tool that shows you what you qualify for. You can take its recommendations and apply them when you file using your preferred method (like TurboTax or a tax professional). It actually does quite well compared to human tax pros in my experience. When I compared its recommendations to what an accountant friend suggested, it found all the same deductions plus a couple my friend missed. The real benefit is that it explains everything in plain English and gives you documentation guidance, which many tax pros don't take the time to do.

Wait, how is this even possible? The IRS phone system is notoriously bad. Are you saying this service somehow jumps the queue or something?

This sounds like a scam. Why would I trust some random service with connecting me to the IRS? Couldn't they be recording my call or stealing my information?

They don't jump the queue at all - they just wait in it for you. It works by using their system to navigate the IRS phone tree and wait on hold, then when a representative is about to answer, they call you and connect the call. It's basically like having someone else sit on hold for you. They don't record your call or have access to your personal information. They're just making the initial connection to the IRS hold queue, then connecting you directly once an agent is available. The actual conversation with the IRS is just between you and the IRS representative. I was skeptical too, but after wasting hours on hold, I was desperate enough to try it and it actually worked.

Thanks for bringing this up! Do you know what the income limits are for Roth IRA contributions? Also, for the SEP IRA, can I contribute to that even if I have a 401k through my main employer?

For 2025, you can fully contribute to a Roth IRA if your modified adjusted gross income is less than $146,000 (single) or $230,000 (married filing jointly). The contribution limit phases out above those amounts until it reaches zero. Yes, you absolutely can contribute to a SEP IRA even if you have a 401k through your employer. The SEP IRA contribution is based only on your self-employment income. The limit is 25% of your net self-employment earnings, up to $69,000 for 2025. It's a great way to reduce taxes on your freelance income while saving for retirement.

HSAs are awesome! Triple tax advantage is right - money goes in tax-free, grows tax-free, and comes out tax-free for medical expenses. For 2025, you can contribute up to $4,150 for individual coverage or $8,300 for family coverage. But you need a qualifying high-deductible health plan to be eligible. Check if your plan is HSA-eligible - the deductible needs to be at least $1,500 for individuals or $3,000 for families.