One thing to also consider is the timing of when your parents actually transfer the property. If they're doing this for estate planning purposes, they might want to consider the current economic climate and property values. Real estate values have been quite high recently, so gifting now while values are elevated could actually be beneficial from a gift tax perspective - they're using up their lifetime exemption based on today's high valuation, but if property values decline in the future, they've effectively "locked in" the gift at the higher value. Also, make sure you understand what happens with things like homeowners insurance during the transfer process. Some policies need to be updated or changed when ownership transfers, even between family members. You'll want to coordinate with your insurance agent to ensure there's no gap in coverage during the deed transfer process. The combination of gift tax implications, capital gains basis issues, property tax reassessment risks, and insurance considerations makes this a complex transaction that really benefits from professional guidance. Good call on setting up those CPA meetings!

Just wanted to add another important consideration that I learned the hard way - make sure to get a professional appraisal of the property at the time of transfer. The IRS requires fair market value to be established for gift tax purposes, and if they ever audit the transaction, having a certified appraisal from a licensed appraiser will protect you. Don't just rely on online estimates or recent comparable sales - those might not hold up if questioned. A proper appraisal typically costs $400-800 but could save you thousands if the IRS ever challenges the reported value and tries to assess additional gift taxes. Also, keep detailed records of any improvements or major repairs your parents made to the property while they owned it. These can sometimes be added to your cost basis even in a gift situation, which would reduce your potential capital gains exposure if you sell later. Your CPA can help determine which expenses qualify for basis adjustments. The documentation requirements for property gifts are much more extensive than most people realize, so starting that paper trail early will make the whole process smoother!

You're definitely on the right track with your thinking! Since you formed your LLC in August, you can absolutely include all your post-formation DoorDash and 1099 editing income as business income. The key is consistency - treat these as legitimate business activities and maintain proper documentation. A few practical tips from someone who made this transition: 1. **Mileage tracking is crucial** - Use an app like MileIQ or Everlance to automatically track your DoorDash miles. This will be one of your biggest deductions. 2. **Business expense deductions** - Don't forget about phone bills (business use portion), car maintenance, tolls, parking fees, insulated bags, phone mounts, etc. These add up quickly. 3. **Quarterly estimated taxes** - With variable gig income, I recommend the "pay as you go" approach. Set aside 25-30% of each payment immediately into a separate tax savings account. This prevents the shock of owing thousands at tax time. 4. **S-Corp election timing** - You're smart to wait on this. Generally, it only makes sense when your business profit exceeds $40-60k annually due to the added compliance costs and complexity. 5. **Record keeping** - Get a dedicated business bank account if you haven't already, and consider a business credit card for expenses. This separation will save you hours during tax prep. The LLC structure gives you flexibility to grow into more complex tax strategies as your income increases. For now, focus on maximizing your legitimate business deductions and maintaining clean books!

The advice here is solid! I just wanted to add one thing that helped me a lot when I was in your exact situation - consider getting QuickBooks Self-Employed or a similar bookkeeping app specifically designed for gig workers and small LLCs. It automatically categorizes your income streams, tracks mileage using your phone's GPS, and even estimates your quarterly tax payments based on your actual earnings. When I was doing DoorDash plus freelance work through my LLC, it saved me hours of manual tracking and made tax time so much less stressful. The app connects to your business bank account and automatically pulls in transactions, then you just need to categorize them as business or personal. It also has a feature that calculates the business use percentage of mixed expenses like your phone bill based on the time you log as "working" in the app. For about $15/month, it basically pays for itself in time saved and helps ensure you don't miss any deductible expenses. Plus it generates all the reports you need for Schedule C filing, which is super helpful when you're new to the business tax world. You're definitely thinking about this the right way though - getting the structure and processes right from the beginning will save you so many headaches later!

I'm going through almost the exact same situation and wanted to share what I've learned after finally getting some answers from the IRS. Like you, I had multiple jobs across states, filed an amended return due to a corrected W-2, and have been waiting 7+ months. Last week I finally got through using the 8am calling strategy (took 3 attempts but it works!) and spoke with an agent who explained what's really happening. When you file an amended return that corrects W-2 information, the IRS has to manually verify the changes with your employer's records in their system. This process can take 4-6 months alone, and that's on top of any initial review time. The agent told me they're severely backlogged in their "wage verification" department specifically. What was really helpful was that she gave me a direct phone number (855-202-4346) for amended return inquiries and a case reference number I can use for future calls. She also confirmed that my refund will include interest calculated from 45 days after my original filing date - in my case, that's adding up to about $400 extra. The most encouraging thing she told me was that returns like ours (multiple jobs + amended W-2s) are actually progressing through the system, just very slowly. She estimated I should see movement in the next 4-6 weeks based on current processing times. I know it's incredibly frustrating, but hang in there. The combination of your situation (multiple states/jobs + stock transactions + amended return) created the perfect storm for delays, but you're definitely not forgotten in the system.

I'm really sorry you're going through this - 6+ months is an incredibly long time to wait for your refund, especially when it's such a significant amount. Your situation resonates with me because I went through something very similar last year. The combination of factors in your case (multiple states, multiple jobs, stock transactions, plus the amended return with corrected W-2) unfortunately creates what the IRS considers a "complex return" that requires manual review. When you filed that amended return in May, it essentially reset the processing timeline because they have to re-verify everything against employer records. I'd strongly recommend trying the congressional representative route at this point. After 6+ months, you're well beyond reasonable processing times, and congressional offices have direct liaison contacts at the IRS who can often get answers when normal channels fail. You just need to fill out a privacy release form on your representative's website. Also, keep in mind that you'll receive interest on your delayed refund calculated from 45 days after your filing date. At the current rate of around 7% annually compounded daily, you're looking at a decent amount of additional compensation by the time your refund comes through. The IRS letters you received are actually a good sign - they indicate normal processing for a complex amended return, even though "normal" feels anything but normal when you're waiting this long. Your return hasn't been forgotten; it's just stuck in a very slow-moving manual verification process. Hang in there - based on everything I've seen, people in your exact situation do eventually get their refunds, it just takes much longer than it should.

Don't forget you can offset those winnings with losses, but only if you have proof! I learned this the hard way. Keep all your ATM receipts at casinos, player's card statements, even hotel bills that show you were there. If you're audited without proof, you're screwed.

Everyone here is giving tax advice but no one mentioned the most important thing - if you won exactly $1200 they probably didn't withhold any federal taxes! The casino is required to give you a W-2G but withholding is only mandatory on slots if you win over $5,000. Make sure you set aside money for taxes so you're not surprised at tax time!

Don't forget to request an abatement of any penalties they've proposed in the CP2000! Since this was your first time dealing with ISOs and you're not trying to hide income (it was on your W-2), you qualify for "reasonable cause" relief from penalties. Include a brief statement saying something like: "I request abatement of any penalties as I made an unintentional error in not reporting the 1099-B. The income was properly reported on my W-2 as shown in the attached documentation, demonstrating there was no intent to underreport income." I was in almost the identical situation in 2020 and not only did they remove the proposed tax adjustment, they also waived all penalties when I explained it was my first time dealing with equity compensation and I didn't understand the dual reporting requirement.

This is a stressful situation but definitely manageable! I went through something very similar with my ISO exercise in 2020. The key thing to understand is that the IRS computer system flagged this because it saw income reported on your 1099-B but couldn't automatically match it to the corresponding W-2 income. When you respond to the CP2000, you'll want to clearly show the connection between your W-2 and 1099-B. Look for Box 14 on your W-2 - many employers specifically note ISO income there, or it might be included in your regular wages in Box 1. Your employer should also have provided an equity statement showing the details of your ISO transaction. A few critical points for your response: 1. Send copies of both your W-2 and 1099-B 2. Include any equity compensation statements from your employer 3. Write a clear explanation showing how the exercise spread was already taxed as ordinary income 4. Calculate any small capital gain/loss from the actual sale price vs. fair market value at exercise 5. Request penalty abatement since this was an unintentional reporting error Don't panic about the deadline - you have options. If you're running short on time, you can call the IRS to request an extension while you gather documentation. The CP2000 is a proposal, not a final assessment, so you have the right to dispute it with proper documentation.