Serious question: has anyone tried faxing? I know it sounds ridiculous, but I've heard some government agencies still prefer fax for some reason. Might be worth a shot?

I've been dealing with this nightmare for 3 months now! What finally worked for me was calling the practitioner priority line (if you have a tax pro helping you) or trying the Spanish language line - I heard they sometimes have shorter wait times and can transfer you to English speakers. Also, try calling on Wednesdays around 10 AM - seems to be less busy than Mondays/Fridays. The whole system is absolutely broken though. We shouldn't have to jump through hoops just to talk to the agency that handles our tax money! 😤

Has anyone considered the rules around "step transaction doctrine"? I've heard the IRS can sometimes claim that direct gifts into an IRA could be viewed as trying to exceed contribution limits if done incorrectly. Would it be safer to just give the money to the grandchild's regular account first?

This is such a thoughtful gift! I went through something similar when helping my adult son with his IRA contributions. The key thing to remember is that the IRS looks at two separate things: 1) whether your grandson has enough earned income to support the contribution (which he clearly does at $85K), and 2) whether the contribution stays within the annual limits. Since money is fungible, it doesn't matter that the $7,000 comes from you rather than his paycheck. Once you gift it to him, it becomes his money to contribute. The IRS won't trace the source of funds in his IRA account. One thing I'd add to what others have mentioned - make sure to keep good records of the gift for your own tax purposes, even though it's well under the annual exclusion limit. It's just good practice to document larger gifts in case there are ever questions down the road. Your grandson is lucky to have someone thinking ahead about his retirement savings at such a young age!

Can I just add that if you're making decent profit through your LLC (like over $40k), you should seriously consider electing S-Corp status? I operated as a disregarded entity for 3 years and was paying wayyyy too much in self-employment taxes. When I switched to S-Corp, I started paying myself a reasonable salary and taking the rest as distributions, which aren't subject to SE tax. Saved almost $6,500 in taxes last year alone!

This is exactly the kind of confusion I had when I started my LLC! The good news is that you're overthinking this - the IRS has pretty clear default rules that work in your favor. Since you have a single-member LLC and never filed any election forms, you automatically have what's called "disregarded entity" status. This means for tax purposes, your LLC doesn't exist as a separate entity - all income and expenses flow directly through to your personal tax return via Schedule C. No Form 8832 needed unless you want to change this default classification. Most small business owners stick with disregarded entity status because it's simpler and avoids the complexity of corporate tax filings. Just make sure you're keeping good records of all business income and expenses throughout the year, and don't forget about self-employment taxes on your profits (Schedule SE). The IRS treats your LLC income as self-employment income, so you'll owe both income tax and SE tax on your net profit. You're definitely on the right track - just report everything on your personal return and you'll be fine!

Has anyone dealt with the AMT implications of selling QSBS? I've heard the excluded portion might still be subject to AMT which could really reduce the benefit.

Great question about QSBS from 1994! Just want to add a couple of important points that others haven't mentioned yet: 1) Make sure to verify your company never converted from C-Corp to S-Corp during your holding period - even a brief S-Corp election can disqualify the shares entirely for QSBS purposes. 2) If you're considering the gift strategy, remember that your daughter would get a "stepped-up basis" equal to the fair market value at the time of gift for gift tax purposes, but she keeps your original 1994 basis for income tax and QSBS calculations. This could create some complexity in her tax planning. 3) One thing to watch out for - if this tech company went through any major restructuring, mergers, or spin-offs over the past 30 years, the QSBS qualification might have been affected. The "same corporation" requirement is pretty strict. Given the age of these shares and potential complexity, you might want to get a tax professional who specializes in QSBS to review your specific situation before making any moves. The 50% exclusion on 30 years of tech stock appreciation could be substantial!

Just want to add another perspective here - I've been dealing with roommate rental income for about 3 years now and learned some things the hard way. One thing that caught me off guard initially was keeping track of improvements vs. repairs. If you fix something that was already broken (like a leaky faucet), that's a deductible repair expense. But if you upgrade something (like replacing old carpet with new hardwood), that's an improvement that has to be depreciated over time instead of deducted immediately. Also, definitely keep receipts for EVERYTHING. I got lazy about it my first year and regretted it when tax time came around. Even small things like furnace filters or light bulbs can add up to meaningful deductions when you're calculating the rental portion. A simple spreadsheet or even just a shoebox works - just make sure you're documenting all your housing-related expenses throughout the year. The percentage calculation Logan mentioned is key too. I calculate mine based on square footage of bedrooms plus shared common areas. So if my roommates have 3 out of 4 bedrooms and we all share the kitchen/living room equally, I use about 62.5% for my rental portion calculations.

Great question! I went through this exact situation when I first bought my house. Yes, you absolutely need to report all $1,950/month ($650 x 3) as rental income on Schedule E, even though it's going toward your mortgage. Here's what helped me get organized: First, figure out what percentage of your home the roommates are using. If they each have their own bedroom and you all share common areas equally, you might calculate it as (3 bedrooms ÷ 4 total bedrooms) + (shared spaces ÷ 4) for your rental percentage. You can then deduct that same percentage of expenses like: - Mortgage interest (not the principal payments though!) - Property taxes - Homeowners insurance - Utilities (if you pay them) - Repairs and maintenance - Depreciation on the rental portion Keep really detailed records from the start - trust me on this. I use a simple Excel sheet to track every house-related expense throughout the year. Even small things like air fresheners or toilet paper can add up when you're calculating your rental portion deductions. The key thing to remember is that while you have to report the income, the deductions will likely offset most or all of it, especially in your first year when you can claim depreciation. Just make sure you're working with the right tax software (you'll need one that handles Schedule E) or consider talking to a tax professional for your first year to make sure you're doing everything correctly.