Will tax software like TurboTax handle this crypto/stock offset correctly? Or do I need something more specialized?

This is exactly the kind of situation where having proper documentation is crucial. I went through something similar last year - had about $8k in stock losses carried forward from 2022 and realized $12k in crypto gains in 2023. The good news is yes, you can absolutely offset them. Both are treated as capital assets on Schedule D. What saved me was keeping detailed records of every transaction - dates, amounts, cost basis, etc. The IRS doesn't care whether your losses came from Apple stock or your gains came from Bitcoin - they're all capital transactions. One thing to watch out for: if you're actively trading both stocks and crypto, make sure you're not running into wash sale rules. The IRS hasn't explicitly applied wash sales to crypto yet, but it's something to be aware of if you're buying and selling similar assets within 30 days. Also, since you mentioned needing an answer "ASAP" - if you're planning to realize those crypto gains before year end, consider the timing. You might want to realize them in smaller chunks to see exactly how much of your carryforward you'll use up, especially if you think you might have more gains or losses next year.

One practical tip I haven't seen mentioned: set up a separate bank account just for your UberEats income and expenses. I drive for multiple delivery apps and this made a HUGE difference in my tax organization. I deposit all app earnings to this account and pay for gas, repairs, etc. from it too. Makes it super easy to track your actual profit without having to sort through personal transactions. Also, save absolutely every receipt related to your deliveries - phone chargers, hot bags, trunk organizers, etc. You'd be surprised what's actually deductible.

Quick warning from someone who's been doing this for 3 years - don't forget about your state taxes too! Everyone talks about federal, but depending on your state, you might need to make estimated state tax payments as well. Also, track your TOTAL mileage for the year (personal + business) so you can calculate the business percentage accurately. So many drivers miss this and it can cause issues if you're audited.

I'm dealing with a similar situation in Germany! One thing that's really helped me is setting up USPS Informed Delivery for my US address (even if it's a mail forwarding service). It emails you grayscale images of the outside of mail pieces that are coming to your address each day. While it doesn't replace getting the actual documents, it at least alerts you when something from the IRS is on the way so you can follow up with your mail service or designated person. You can see if it looks like an important notice based on the envelope format - IRS notices usually have a distinctive look. Also, make sure to update your address with the IRS using Form 8822 if you haven't already. Even if you're using a forwarding service, having your current international address on file as a backup can sometimes help if there are delivery issues with your primary US address.

As a US expat who dealt with this exact issue while living in Australia, I understand your frustration completely. The reality is that the IRS is still very much a paper-based system for most official communications, but there are some workarounds that have saved me countless headaches. First, definitely sign up for an IRS online account - while it won't email you notifications, you can proactively check for transcripts and some notices. Second, I highly recommend using both Form 8821 (for information sharing) and potentially Form 2848 (power of attorney) with a trusted person in the US who can act quickly if needed. The virtual mailbox services mentioned here are absolute lifesavers. I use one that provides same-day scanning and can even deposit checks for you. The key is finding one that's experienced with financial and tax documents - not all mail services handle sensitive documents properly. One thing I learned the hard way: always respond to IRS notices in writing and keep copies. Even if you call them (using something like Claimyr to avoid the hold times), follow up with written correspondence to create a paper trail. The IRS operates on documentation, not phone conversations. Don't let the stress get to you - with the right systems in place, you can manage this successfully from abroad!

Im curious if anyone knows about the deadline for making the SEP contributions? Is it the tax filing deadline (april 15) or the extended deadline if you file an extension?

Just wanted to add a quick note about timing - since you mentioned tax season coming up fast, remember that you have until your business tax filing deadline (including extensions) to make your 2024 SEP IRA contribution. So even if you file your personal return by April 15th, you can still make the contribution later if your S-Corp files an extension. Also, make sure your payroll records are clean for calculating that W-2 wage base. I learned the hard way that bonuses, overtime, and other compensation all count toward the SEP calculation, but things like health insurance premiums paid by the company and other fringe benefits don't. One more thing - if you have any other employees (even part-time), you'll need to contribute the same percentage of their compensation that you contribute for yourself. This can get expensive quickly, which is why the Solo 401(k) mentioned above might be worth exploring if it's just you.

I'm dealing with this exact same situation right now! My Colorado refund was marked as mailed on April 8th, so I'm at day 8 and getting a bit anxious too. Reading through all these experiences has been incredibly helpful - it's reassuring to see that 10-17 days seems to be the normal range for most people. What really stood out to me is the suggestion about checking with your local post office around day 12. I never would have thought of that, but it makes perfect sense that they might have insights about local delivery delays that the state wouldn't know about. I'm also planning to wait until the 15 business day mark before contacting Colorado DOR, based on what everyone here has shared. One thing I learned from this thread is to definitely switch to direct deposit next year - 5 days versus 2-3 weeks is a no-brainer! But for now, it sounds like we just need to practice patience. Thanks for starting this discussion, it's really helped calm my nerves about the timeline.

I'm going through the exact same thing right now! My Colorado state refund was marked as mailed on April 10th, so I'm only at day 6 but already starting to feel anxious about it. This thread has been incredibly reassuring though - seeing that most people are getting their checks within 10-17 days after the mail date really helps put things in perspective. What I find most helpful from reading everyone's experiences is that there seems to be a clear pattern: the state is reliable about actually mailing the checks, but USPS delivery times are just really variable right now. The suggestion about checking with your local post office around day 12 is something I definitely plan to try if I don't receive mine by then. I'm also kicking myself for not choosing direct deposit this year - 5 days versus potentially 3 weeks is such a huge difference! But for now, it sounds like patience is key. Thanks to everyone who shared their timelines and experiences - it really helps to know this is normal processing time and not something to panic about yet.