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.

I went through a similar situation last year and the confusion around Publication 936 is totally understandable - it's written in such dense tax language! Based on everything I researched and confirmed with my tax preparer, you should be able to deduct that mortgage interest. The key thing that works in your favor is that you used the cash-out refi proceeds specifically to purchase another residence, which keeps it classified as acquisition debt rather than home equity debt under the Tax Cuts and Jobs Act rules. Since the second property qualifies as your second home (your son living there as your dependent actually supports this, plus your personal use through visits), the interest should be fully deductible as long as you're under the $750,000 qualified residence debt limit. I'd definitely recommend keeping a simple log of your visits to the second property - just dates and brief notes like "family weekend" or "maintenance visit." This creates documentation showing consistent personal use if the IRS ever has questions. Also make sure you have clear records showing how the refinance proceeds went directly to purchasing the second home. Since this deduction would push you into itemizing and make a significant difference in your tax situation, it's probably worth a consultation with a tax professional who handles real estate transactions just to double-check everything. But based on your description, this seems like a straightforward case where the interest should be deductible.

After reading through all these helpful responses, I think you're in a strong position to deduct that mortgage interest! Your situation hits all the key requirements: the cash-out refi proceeds were used to acquire another qualified residence, your son's use as your dependent counts as personal use by you, and you maintain regular personal visits to establish it as your genuine second home. The most important thing is making sure you can document the direct flow of funds from your refinance to the second home purchase - keep those closing statements organized to show the clear money trail. Since you paid off your primary home before doing the cash-out refi, you're likely well under the $750,000 qualified residence debt limit too. I'd also echo what others have said about starting a simple visit log now if you haven't already. Just basic entries like "weekend visit - family time" or "3-day stay for maintenance" will help establish that pattern of personal use if the IRS ever has questions. Given that this deduction would push you into itemizing and create significant tax savings, it's definitely worth pursuing. The rules can seem complex, but based on everything you've described, this appears to be exactly the type of situation where mortgage interest remains deductible under current tax law. Just make sure to keep detailed records and consider that professional consultation for peace of mind given the dollar amounts involved.

I went through a nearly identical situation with Jackson Hewitt in 2022 - they botched my education credits and completely missed my student loan interest deduction, costing me almost $1,200 in additional tax liability. Here's what actually worked for me: 1. **Document everything with dates and reference numbers** - I created a spreadsheet tracking every phone call, email, and document exchange 2. **Request their internal complaint escalation process** - Most people don't know that Jackson Hewitt has a formal Quality Review Department separate from local management 3. **File Form 14157 immediately** - Don't wait. I filed mine while simultaneously working with their corporate office, which actually strengthened my position 4. **Contact your state's Board of Accountancy** - If your preparer was a CPA or EA, this adds serious pressure The breakthrough came when I sent a certified letter to their corporate Quality Review Department (not just customer service) citing IRC §6694 and mentioning I had already filed Form 14157. Within 5 business days, I had a call from their regional compliance manager who arranged for a senior EA to completely redo my return at no cost. They also reimbursed the $89 I paid for professional review of their errors. Total timeline: 3 weeks from escalation to resolution. The key is being persistent and showing you understand the regulations better than their seasonal preparers do.

Based on my experience dealing with tax preparer errors, I'd recommend taking a multi-pronged approach while the filing deadline is still fresh. First, send a demand letter via certified mail to both the local office manager AND Jackson Hewitt's corporate compliance department, specifically referencing IRC §6694 and Circular 230 violations. Include calculated damages from their errors and request full remediation within 10 business days. Simultaneously, file Form 14157 with the IRS - don't wait on this. The form creates an official record and often motivates preparers to resolve issues quickly. Also consider contacting your state's consumer protection agency if Jackson Hewitt is licensed there. Document the specific financial impact: if their education credit error cost you $1,000 in additional tax, plus any penalties or interest, they should cover those costs under their accuracy guarantee. Most major chains will settle rather than face regulatory scrutiny, especially when you demonstrate knowledge of the specific tax code sections they violated. Keep pushing up their corporate ladder - local managers often lack authority to authorize full remediation, but regional compliance departments usually do. The key is showing you won't accept partial fixes or excuses.

One important thing no one's mentioned yet - if your parents receive Medicaid, SSI, or certain other benefits, being claimed as dependents on your taxes could potentially affect their eligibility or benefit amounts. Some means-tested government programs have specific rules about this. I found this out the hard way when I claimed my grandmother and it caused issues with her benefits. Might be worth checking with your state's Medicaid office or your parents' benefits administrators before making any changes to your tax situation.

This is really helpful information everyone! I'm dealing with a similar situation but with one additional wrinkle - my parents also receive some help from my brother who lives across the country. He sends them about $300/month to help with their medications and other expenses. Does anyone know how this affects the "more than half support" calculation? I'm definitely paying the majority of their living expenses (housing, utilities, food), but I want to make sure I'm calculating this correctly. Do I need to include what my brother contributes when determining if I'm providing more than half their total support? Also, has anyone dealt with the IRS asking for documentation of the support you provide? I've been keeping receipts like Molly mentioned, but wondering what specific records I should focus on maintaining.

Has anyone had experience with the 10-year rule for inherited annuities? My spouse inherited an annuity and we're trying to figure out if we need to take all the money within 10 years or if different rules apply for non-spouse beneficiaries?

I went through something very similar when I inherited my father's annuity last year. The key thing that helped me was understanding that you need to look at Box 7 on your 1099-R for the distribution code - this tells you exactly how the IRS expects it to be reported. For inherited annuities, you'll typically see code "4" which indicates a death benefit distribution. In TurboTax, when it asks about qualified vs non-qualified, since this was likely a personal annuity your mom bought (not through an employer plan), it's probably non-qualified. The tricky part is the basis calculation. Since you mentioned she opened it in 1997, there's likely been significant growth over the years. If Prudential shows the full amount as taxable on the 1099-R, I'd definitely recommend calling them to ask about the original investment amount (cost basis) like others have suggested. This could save you thousands in taxes. Also, make sure you understand that this will be taxed as ordinary income, not capital gains, so it could potentially bump you into a higher tax bracket depending on your other income. You might want to consider if there are any tax planning strategies for next year to offset this additional income.