One thing to consider is the timing of when your son plans to sell these investments. Since he'll inherit your cost basis (what you originally paid ~14 years ago), he'll owe capital gains tax on the full appreciation when he sells. Given that the investments have grown from $9,000 to $105,000, that's potentially significant capital gains tax. If he's planning to hold these investments long-term anyway, the gift approach works well. But if he wants to liquidate soon after receiving them, you might want to factor in the tax impact on his side. Sometimes it makes sense to sell some positions while they're still in your names (especially if you're in a lower tax bracket) and gift the cash proceeds instead, depending on your respective tax situations. Also, make sure your brokerage can handle the transfer properly with correct basis reporting. Some brokers are better than others at tracking gifted securities and providing the right tax documents.

You're dealing with a common but tricky situation. The good news is that gifting stocks directly to your son won't trigger capital gains for you - it's not considered a taxable event for the giver. However, your son will inherit your original cost basis (around $9,000), so he'll owe capital gains tax on the full $96,000 appreciation when he eventually sells. Given the $105,000 value, you have two main paths: 1) **Spread it over 3 years**: Gift $38,000 worth of shares annually (you and your wife each using your $19,000 annual exclusion). This avoids any gift tax paperwork entirely. 2) **Transfer everything at once**: You'd need to file Form 709 for the amount over $38,000, but likely wouldn't owe actual gift tax unless you've already used up significant portions of your lifetime exemption ($13.99 million per person in 2025). Before deciding, definitely check what tax bracket your son is in for capital gains. If he's in a higher bracket than you are, it might actually be more tax-efficient to sell some of the most appreciated positions while they're still in your names, then gift the proceeds. This strategy works especially well if you're in the 0% or 15% long-term capital gains bracket. Also, make sure your brokerage can properly document the gift with correct basis reporting for future tax filings.

Another expense to consider - property taxes during the renovation period. Unlike loan interest and utilities which can potentially be capitalized, property taxes are generally deductible on Schedule A (if you itemize) rather than being added to basis. This is true even during the renovation period. Also, make sure you're separating any personal use from the renovation timeline. If you stayed in the property at any point during renovations, you'll need to allocate expenses accordingly. The IRS is pretty strict about this - only expenses incurred while the property was held purely for investment/sale purposes can be capitalized. One last tip: keep photos documenting the before/during/after condition of the property. This helps support your position that certain expenses were truly improvements rather than just repairs or maintenance.

One thing that hasn't been mentioned yet - if you had to get any permits for your renovation work, those permit fees can definitely be added to your basis as they're directly related to the improvements. Same goes for any required inspections. Also, be careful about mixing renovation expenses with regular maintenance. For example, if you had to replace a broken window during renovation, that's maintenance/repair. But if you upgraded all the windows to energy-efficient ones as part of improving the property, those are capital improvements that increase your basis. The key test is whether the expense restores the property to its original condition (repair/maintenance) or makes it better than it was (improvement). For a flip, you're generally trying to improve the property beyond its original state, so most of your major expenses should qualify for basis treatment. Keep all your receipts organized by category - it'll make everything much easier come tax time!

The community property states are Arizona, California, Idaho, Louisiana, Nevada, New Mexico, Texas, Washington, and Wisconsin. If you're in any of these, these signature rules apply! Also, I've found that using good tax software makes a huge difference. Anyone have recommendations for S-Corp specific software that handles these community property issues well?

I'm dealing with this exact situation right now in New Mexico! My CPA told me that even though my LLC operating agreement states the business is my separate property, the IRS still typically requires both spouses to sign Form 2553 in community property states unless you have very specific documentation. What I learned is that you need more than just language in your operating agreement - you typically need either a formal property agreement filed with the state, a spousal consent form acknowledging separate property status, or clear documentation that the business was formed with separate property funds (like inheritance or pre-marital assets). Since your deadline is approaching and your accountant is unavailable, I'd recommend having your husband sign the consent section to be safe. You can always consult with your accountant later about whether additional documentation might help with future filings, but missing the S-Corp election deadline would be much worse than having an "unnecessary" signature. The IRS tends to be very conservative about these community property issues, so when in doubt, include the spouse signature!

Your situation is actually pretty common, and the answer is clear - if you're married and filing a joint return with your spouse, you cannot be claimed as a dependent on your mom's tax return. The IRS Joint Return Test specifically prevents this, regardless of who paid for your education expenses. However, there's an important point about your spouse's documentation that others have mentioned. If your spouse doesn't have an SSN yet, you'll need to get an ITIN (Individual Taxpayer Identification Number) to file jointly. This requires submitting Form W-7 with your tax return, and the process can take 7-11 weeks. Given the timing, you might want to file an extension to avoid missing the deadline. As for your mom, she may still be able to claim education credits for the tuition she paid directly to your school, even without claiming you as a dependent. The Lifetime Learning Credit or American Opportunity Tax Credit might be available to her if she meets the income requirements. This could be a good compromise - she gets some tax benefit for helping with your education, but you still file correctly with your spouse. I'd suggest having a calm conversation with your mom explaining that this isn't about choosing sides, but about following tax law correctly. Her accountant should understand these rules, and if they don't, that's concerning.

I went through this exact same situation two years ago when I got married! My dad was insisting his accountant could claim me as a dependent even though I was married filing jointly, and it caused a huge family argument. The bottom line is that the IRS rules are very clear on this - if you're married and filing a joint return, you cannot be claimed as a dependent by anyone else. Period. The Joint Return Test is one of the qualifying tests for dependency, and filing jointly automatically disqualifies you. What helped resolve things with my family was explaining that this wasn't about me choosing not to help them with taxes - it's literally against federal tax law. Your mom's accountant should absolutely know this rule, and if they don't, that's a red flag about their competence. The good news is that your mom can still benefit from paying your tuition! She can likely claim education credits directly (like the American Opportunity Tax Credit or Lifetime Learning Credit) for expenses she paid to your school, even without claiming you as a dependent. This might actually be better for her tax-wise anyway. I'd suggest sitting down with your mom and maybe even offering to help her find a more knowledgeable tax preparer if her current accountant is giving incorrect advice about such a basic dependency rule.

Has anyone actually tried telling the IRS they just don't have the money? Like what happens if you literally can't pay?

I went through something similar last year - owed about $11k in self-employment taxes and was frantically looking for ways to reduce it. Unfortunately, as others have mentioned, charitable donations won't help with your current tax debt since they're deductions, not credits, and they only apply to future tax years anyway. What helped me was actually going through all my business expenses with a fine-tooth comb to make sure I hadn't missed any legitimate deductions when I originally filed. Things like home office expenses, business meals, professional development courses, even subscriptions to industry publications - it all adds up. I ended up finding about $2,800 in deductions I had overlooked and filed an amended return. For the remaining balance, I set up a payment plan with the IRS. The monthly payment was much more manageable than trying to come up with the lump sum, and the penalties/interest weren't as bad as I expected. The key is to contact them before they start collection actions - they're actually pretty reasonable to work with if you're proactive about it.