Another option I don't see mentioned - check if your potential new employer offers an HDHP option you could enroll in immediately upon starting. Many employers have waived waiting periods for benefits during the pandemic and some have kept those policies. If your current coverage ends October 15th and new employer coverage can start October 16th, that would satisfy the continuous coverage requirement. Just make sure the new plan qualifies as an HDHP for HSA purposes - not all high-deductible plans do!

I want to add one more consideration that might be helpful - if you're planning to leave around October 15th specifically, you might want to think about pushing it to November 1st instead. Since HSA eligibility is determined by having HDHP coverage on the first day of the month, leaving mid-month in October could make you ineligible for the entire month of October. If you leave on October 15th and there's any delay getting new coverage started, you'd lose October eligibility even if you only had a few days gap. But if you can wait until November 1st, you'd maintain full October eligibility and then just need to ensure your new HDHP coverage starts November 1st with no gap. I know job timing isn't always flexible, but even a couple weeks could make a significant difference for your HSA testing period compliance. The penalties for breaking the testing period can be substantial, so it might be worth exploring if your departure date has any flexibility.

The Wisconsin Department of Revenue website has a good section on reciprocity agreements and tax credits for taxes paid to other states. You can find it under their "Nonresident and Part-Year Resident" section. Generally, Wisconsin allows credits for income taxes paid to other states, which can significantly reduce your overall burden. For researching reciprocity by state, the Federation of Tax Administrators has a useful chart showing which states have reciprocal agreements, though it's more helpful for wage income than partnership income. For partnership-specific rules, you'll likely need to check each state's tax department website individually. One thing I learned the hard way - some states have "safe harbor" provisions for small amounts of partnership income (usually under $1,000-$3,000 depending on the state) where you don't need to file even if income is technically sourced there. Colorado itself has such provisions for non-resident partners in certain situations. Since your partnership involves active property management, I'd definitely recommend getting that state-by-state breakdown before making any filing decisions. The nature of the activity can completely change your obligations, and it sounds like you're in a similar situation to what I dealt with. Better to get the details upfront than deal with amended returns later!

As someone who's been through the multi-state K-1 reporting maze multiple times, I want to add a few practical tips that might save you some headaches: First, create a simple spreadsheet tracking all your K-1 income by state and type (rental vs. business operations). This becomes invaluable when you're trying to figure out minimum filing thresholds and potential credits. I wish I had started doing this from year one instead of trying to reconstruct everything later. Second, don't assume your partnership's tax preparer has communicated state filing requirements clearly. I've found that many partnerships focus primarily on federal reporting and provide minimal guidance on state obligations. It's worth having a direct conversation with their tax team about composite filing elections and state-specific reporting. Third, if you do end up filing in multiple states, consider the timing carefully. Some states process non-resident returns much slower than others, and if you're expecting refunds, the delays can be significant. Florida and Texas won't be an issue since they don't have personal income taxes, but other states in future years might be. Finally, keep detailed records of any state taxes you do pay. Wisconsin's credit for taxes paid to other states can be quite generous, but you need proper documentation. The credit can sometimes result in a net tax benefit if the other state's rates are higher than Wisconsin's. The key is getting organized upfront rather than scrambling at filing time. These multi-tiered partnership situations are becoming more common, so developing a systematic approach will serve you well in future years.

This thread has been absolutely invaluable! I'm in such a similar situation - received about $2,300 through Apple Pay last year and was completely stressed about whether I needed to report it or not. Like everyone else here, most of my transactions were personal - friends paying me back for group dinners and shared Uber rides, selling some old gaming equipment and furniture when I moved (definitely at a huge loss compared to what I originally paid), and a couple small payments for house-sitting for neighbors while they were out of town. Reading through all these incredibly detailed responses has finally given me clarity on the key distinction between personal transactions versus actual business income. The equipment/furniture sales at a loss and friend reimbursements clearly aren't taxable, but those house-sitting payments should definitely go on Schedule C since they were compensation for services, even though the amounts were small. I had no idea there wasn't a minimum threshold for reporting self-employment income - that's such crucial information! And the clarification about the current $20,000 AND 200 transactions threshold still being in effect (rather than the delayed $600 threshold) has been really helpful for understanding the 1099-K situation. I'm absolutely going to implement everyone's advice about keeping better records going forward. Adding quick notes like "Jake's half of pizza" or "house-sitting for the Martins" as transactions happen is such a simple solution that could prevent all this anxiety next year. Thank you to everyone who shared their experiences, knowledge, and even those helpful service recommendations! This community has been such a lifesaver for navigating these confusing payment app tax situations. You've all helped me feel so much more confident about handling my taxes correctly.

This entire discussion has been incredibly helpful! I'm in almost the exact same situation as everyone else here - received about $2,500 through Apple Pay last year and was completely panicking about tax implications. Like so many others, most of my transactions were personal - friends paying me back for group concert tickets and shared dinners, selling some old furniture and electronics when I downsized apartments (definitely sold everything at a loss), and a few small payments for doing some freelance graphic design work for local small businesses. Reading through all these detailed responses has really clarified the key distinction that everyone keeps mentioning - personal transactions versus actual business income. The furniture/electronics sales at a loss and friend reimbursements clearly aren't taxable based on all the experiences shared here, but I definitely need to report those design payments on Schedule C even though they were relatively small amounts. Learning that there's no minimum threshold for reporting self-employment income was a real eye-opener! And the clarification about the current $20,000 AND 200 transactions threshold still being in effect has been super helpful for understanding why I didn't receive any 1099-K forms. I'm absolutely going to start keeping better records going forward using everyone's note-taking suggestions. Adding quick descriptions like "Mike's share of dinner" or "logo design for coffee shop" when transactions happen seems like such a simple solution to avoid this stress next year. Thanks to everyone who shared their experiences and knowledge! This community has been such a valuable resource for navigating these confusing payment app tax situations. It's so reassuring to know that most of us were dealing with the same concerns and that the solutions are much more straightforward than we initially thought.

Something else to keep in mind is the potential impact on your overall asset allocation. When you sell and rebuy stocks to reset your cost basis, you might be out of the market for a brief period (even if it's just minutes), and during volatile times this could affect your portfolio balance. I'd recommend reviewing your target allocation before executing this strategy. If you're planning to reset cost basis on a significant portion of your equity holdings, consider whether you need to rebalance other positions at the same time to maintain your desired asset mix. Also, make sure you have enough cash available in your account to rebuy immediately after selling. The last thing you want is to have your sale settle and then discover you can't rebuy right away due to settlement timing or insufficient funds, especially if the stock starts moving up while you're waiting.

This is a solid tax strategy that I've used successfully myself. Just want to emphasize a few key points that others have touched on: 1. **Documentation is crucial** - Keep detailed records of your original purchase dates, sale dates, and repurchase dates. You'll need this for future tax calculations, especially to track holding periods for long-term vs short-term treatment on future sales. 2. **Consider your overall tax picture** - Make sure you're not pushing yourself into a higher tax bracket by realizing all these gains at once. Sometimes it makes sense to spread this strategy over multiple tax years. 3. **Transaction costs matter** - Don't forget to factor in brokerage fees when calculating whether this strategy makes financial sense, especially for smaller positions. 4. **Review quarterly** - I've found it helpful to reassess this strategy quarterly rather than just once per year, as your loss carryovers and current year gains/losses can change significantly throughout the year. The strategy absolutely works from a tax perspective - just make sure the execution aligns with your broader financial goals and risk tolerance. Good luck!

I went through the exact same thing last year with my W-2! My employer uses ADP Total Source as their PEO, and I was completely panicked when I saw their name and EIN instead of my actual company's information. I spent way too much time researching this online and even called my tax preparer in a panic. Turns out it's completely legitimate - PEOs like BBSI, ADP, Insperity, etc. are required to issue W-2s under their own EIN since they're handling all the payroll tax obligations. The key thing that helped me feel confident about filing was realizing that the IRS computer systems are expecting to see the PEO's information because that's who's been making the quarterly tax deposits and filing the employment tax returns all year. If you tried to use your wife's actual employer's EIN instead, it would create a mismatch in their system. Just file exactly as the W-2 shows and you'll be fine. This arrangement is actually becoming more and more common as small businesses outsource their HR and payroll functions to these professional employer organizations.

I work in payroll for a mid-sized company and can confirm everything others have said - this is completely normal! When your employer uses a PEO like BBSI, they're essentially "leasing" employees to the PEO for tax purposes while maintaining the actual employment relationship. One additional thing to keep in mind: if your wife ever needs to provide employment verification for things like mortgage applications or background checks, she should use her actual employer's information (the marketing firm), not BBSI's. The PEO relationship is purely for payroll and benefits administration. Also, don't be surprised if you see BBSI's name on other tax documents too, like her 401(k) statements if they manage the retirement plan. This is all part of the same arrangement and nothing to worry about!