2 This might be a dumb question but do I need to make quarterly estimated payments on self-employment tax too or just on income tax?

Just to add another perspective - I've been self-employed for about 5 years now and this confusion about SE tax vs income tax trips up almost everyone in their first year. One thing that really helped me was setting up a separate savings account specifically for taxes and automatically transferring about 30% of every payment I receive. This covers both the self-employment tax (around 14% after the deduction for the employer portion) plus income tax. It's better to overestimate and get a refund than to be short come tax time. Also, don't forget that you can deduct half of your self-employment tax when calculating your income tax - it's like getting back the "employer portion" since you're paying both sides as a self-employed person. The tax software handles this automatically but it's good to understand why your taxable income gets reduced.

Don't forget there are different rules depending on your business structure! If you're an S-corp and you own more than 2% of the company, the rules for health insurance deductions work differently than what everyone's discussing here. For 2%+ S-corp shareholders, the company can pay the premiums but they have to be included in your W-2 as wages (Box 1), but then you can take the self-employed health insurance deduction on your personal return. Just wanted to throw that out there because I got audited last year for doing this wrong!

Quick tip for anyone offering health insurance - make sure you're filing Form 1095-B/1095-C as required for ACA compliance if you have the right number of employees! The rules about which employers need to file these forms are super confusing but the penalties for not filing are brutal. My company got hit with a $3,200 penalty last year because I didn't know we needed to file these!

Your dad's situation is definitely fixable, but time is critical here. I agree with the advice to apply for Social Security immediately - don't wait for the tax situation to be resolved first. The SSA can work with his earnings record that employers have been reporting all these years. For the tax side, start by requesting wage and income transcripts from the IRS for all the unfiled years. You can do this online at irs.gov or by calling them (though as others mentioned, getting through can be challenging). These transcripts will show what income was reported by his employers and any taxes withheld. Since he had taxes withheld from his paychecks, he likely doesn't owe anything and may even be due refunds for some years. The key is getting those last 6 years filed to bring him into compliance. Given the complexity and the urgency with his health situation, I'd strongly recommend working with a tax professional who has experience with unfiled returns - they can streamline the process and help avoid costly mistakes. The most important thing is to take action now rather than letting this drag on any longer. Both his Social Security benefits and potential tax refunds are time-sensitive.

I went through almost the exact same situation with my father-in-law two years ago. He hadn't filed in about 18 years and was panicking about Social Security eligibility. Here's what we learned that might help: First, definitely start the Social Security application ASAP as others have mentioned - the earnings record from employers is what matters most for benefits, not tax filings. We were amazed to discover his full work history was already in their system from employer reporting. For the IRS side, we found out that since taxes were withheld from his paychecks the whole time, he actually qualified for what's called "substitute for return" status for many years where the IRS basically filed simplified returns on his behalf. This meant he wasn't in as much trouble as we feared. The real breakthrough came when we got his wage and income transcripts for all the missing years. It showed that for 4 of the years, he was actually owed refunds totaling over $3,200 (though we could only claim the ones from the last 3 years). We ended up only needing to file the last 6 years to get him current, and the whole process took about 3 months working with a tax professional who specialized in unfiled returns. The key was getting started immediately - don't let fear of the IRS paralyze you into waiting longer. Your dad's health situation makes this urgent, but it's absolutely manageable. The government actually wants people to get caught up and claim their benefits!

I'm a former banking operations specialist, and there may be some additional factors at play here. Chase, like most large banks, typically processes ACH transfers in batches, usually around 2-3 times per day. If the IRS transmission occurred after the final batch on 3/19, it would likely be processed the following business day. Additionally, there could possibly be a security hold if this is a new account, if the amount is significantly larger than previous deposits, or if there have been recent account changes. These holds are generally 2-3 business days but can extend to 5 business days in some circumstances.

I'm dealing with this exact same situation right now! My DDD was 3/19 with Chase and I'm still waiting too. After reading all these responses, I called Chase this morning using the advice from @Lucy Taylor about calling the direct deposit department specifically. The rep told me they can see a "processing deposit" from the Treasury that should post within 24-48 hours. She said it's been in their system since 3/20 but got flagged for their standard tax refund verification process. Apparently this is happening to a lot of Chase customers with DDDs from 3/19. Really frustrating that they don't show these as pending in online banking! I'll update once it hits my account.

Has anyone used TurboSelf-Employed for handling these kinds of business loan situations? I can never figure out where to enter loan proceeds vs. payments in the software and always worry I'm doing it wrong.

As someone who went through a similar learning curve with my consulting business, I'd recommend getting clear on the fundamentals before making any moves. The IRS treats loan proceeds and business expenses as completely separate things. Your $65k profit is taxable income period - doesn't matter if you use it to pay off loans, buy a yacht, or stuff it under your mattress. But here's what CAN help: if you have legitimate business expenses you were planning to make anyway (equipment, software, marketing, inventory), financing those purchases can preserve your cash flow while creating deductions. The wealthy don't avoid taxes by shuffling loan payments around - they strategically time business investments and use debt to acquire income-producing or depreciable assets. Big difference between that and trying to make loan repayments count as expenses (which they're not). My advice: talk to a tax professional about legitimate business investments you could make before year-end that would qualify for Section 179 or bonus depreciation. That's where the real tax savings come from, not from loan gymnastics.