Keep in mind the $20k threshold for Cash App (and most other payment processors) changed recently. For 2022 tax year it was $20k AND 200 transactions, but for 2023 tax year it was supposed to be $600, then they postponed that. Double check the current threshold so you know what to expect!

This is really helpful info everyone! I'm in a similar boat but with PayPal instead of Cash App. One thing I learned the hard way is to keep really detailed records of what each payment was for, especially if you're mixing business and personal use of these apps. The IRS wants to see that these were legitimate business expenses, so I started keeping screenshots of the payment descriptions and matching them to invoices or work orders. Makes the whole 1099 process way smoother when you have everything organized from the start instead of trying to piece it together later. Also agree 100% on getting that W-9 ASAP - I had one contractor who gave me wrong info and it was a nightmare to fix after I'd already filed. Better to verify everything now while there's still time!

Something no one mentioned yet - make sure you and your spouse don't accidentally exceed the family limit COMBINED during the transition months. When my husband and I went through this, our benefits department counted wrong and we over-contributed by accident. Had to withdraw the excess contribution before filing taxes which was a hassle because we'd already spent some of the HSA funds on medical expenses. Just double check all your calculations!

This is such a timely question! I just went through something similar when my partner switched jobs mid-year. One thing that really helped me was keeping detailed records of exactly when each coverage period started and ended - down to the specific dates, not just months. The IRS can be pretty strict about the timing, especially if there are any gaps in coverage or overlapping periods. I'd recommend documenting everything: when your wife's current coverage under your plan ends, when her new employer's coverage begins, and whether there's any continuation coverage (like COBRA) in between. Also, don't forget about the catch-up contributions if either of you is 55 or older! Those rules can get even more complex with mid-year changes. The additional $1,000 catch-up contribution follows the same monthly calculation rules, so you'd need to factor that in too. One last tip - consider setting up automatic contributions to match your calculated monthly limits rather than trying to make one large contribution at year-end. It helps avoid accidentally over-contributing and makes the whole process much more manageable.

I've been dealing with IRS phone systems for years, and sometimes the Practitioner Priority Service line can work even for non-practitioners. Try 866-860-4259 and when prompted, select the option for tax professionals. You might get transferred a few times, but I've found agents are sometimes willing to help even when you're not a tax pro. I did this last year when my client's return was stuck in processing purgatory. Just be polite and explain your situation clearly.

I'm going through the exact same nightmare right now - filed 1/24 and still nothing on transcripts or WMR. After reading through all these suggestions, I'm going to try the 866-682-7451 ext 569 route first thing tomorrow morning. The idea of paying $20 for a callback service is tempting, but I think I'll exhaust the free options first. Has anyone had success with the local IRS Taxpayer Assistance Centers? I know they're appointment-only now, but wondering if that might be another avenue when the phones keep failing us. This whole situation is so frustrating - we shouldn't have to jump through these hoops just to get basic information about our own tax returns!

Did you have to call them or did it just randomly resolve itself?

Wow, congratulations on finally getting your refund! That's such a relief after waiting so long. I'm still stuck in verification hell with my EITC - been waiting since March. Did you have to submit any additional documentation when you amended to remove the credits, or was it pretty straightforward? I'm considering doing the same thing at this point because the wait is killing me 😩

Has anyone actually successfully qualified for trader tax status while doing swing trading? I'm holding positions for about 2-3 weeks on average, making maybe 6-8 trades per week. My tax guy says I'm nowhere near the volume needed, but then I read about others claiming trader status with similar patterns.

The consensus here is spot on - swing trading with your holding periods typically won't qualify for trader tax status or provide the tax benefits you're hoping for with an LLC or S-Corp structure. However, there's one angle that hasn't been fully explored: if you're planning to scale up your trading activities significantly in 2025, it might be worth considering the entity structure now to avoid complications later. The administrative burden of transferring existing positions from individual to business accounts can be substantial. That said, at your current activity level, you're likely better off focusing on maximizing the deductions you can already take as an individual investor - things like investment advisory fees, research subscriptions, trading software, and a portion of your home office if used exclusively for trading research. The real question is whether you see your trading evolving into something more substantial where you'd eventually meet the criteria for trader tax status. If not, the entity formation is probably an unnecessary expense and complication for your current situation.