Has anyone used TurboTax for reporting gambling winnings? Does it walk you through the process well or should I use a different tax software?

One thing I'd add that hasn't been mentioned yet - keep ALL your receipts from the casino, not just the W-2G forms. This includes ATM receipts, food/drink receipts, parking receipts, even hotel receipts if you stayed overnight. These help establish a timeline and can support your gambling activity documentation. Also, consider opening a separate bank account just for gambling if you plan to do this regularly. It makes tracking so much easier come tax time. You deposit your gambling bankroll, withdraw winnings, and everything is cleanly separated from your regular finances. And remember - gambling winnings are subject to both federal AND state taxes in most states, so don't forget to check your state's specific requirements. Some states have different thresholds for reporting than the federal government.

3 One thing nobody mentioned - make sure you keep a copy of that W9 form you filled out. I had an issue where my former landlord sent me a 1099 with incorrect information because they messed up entering my SSN from the W9. It was a huge hassle to fix, and having my copy of the form helped prove I gave them the correct info.

Great discussion everyone! As someone who's dealt with this exact situation, I wanted to add that it's also worth checking if your state has any specific requirements about when landlords must pay out accrued interest. Some states require annual interest payments to tenants, while others only require it at the end of the lease. This can affect when you'd receive a 1099-INT - you might get one each year if they pay interest annually, or just one big form when you move out if they hold it until lease termination. Your lease agreement should specify which approach your landlord uses. Also, keep in mind that even small amounts of interest income need to be reported on your tax return, regardless of whether you receive a 1099-INT form.

I just went through this process myself! One important thing to note - while the SECURE Act 2.0 does extend the ESTABLISHMENT deadline to your tax filing date, there are still some practical considerations about CONTRIBUTIONS. If you're planning to make employee deferrals (the part that comes out of your own compensation), you technically need to have determined those amounts before the end of the calendar year. The employer contribution part (the 25% of net earnings) can be contributed up until your tax filing date. So while you CAN set up the plan in 2025 for 2024, you might be limited to just the employer contribution portion depending on how your plan provider handles this. Different providers have different interpretations of how this all works with the new rules.

Has anyone used Fidelity for their Solo 401k? I'm trying to decide between them and Vanguard for my photography business. Also wondering if anyone knows if these providers are fully updated on the SECURE Act 2.0 changes regarding the setup deadlines?

Did you check if your spouse's SSN was used instead of yours when making the payment? That's what happened to me with our joint return. The payment was showing up under my wife's account but not mine, even though I was the primary taxpayer. Such a stupid system that they can't link payments between spouses on joint returns!

Great news that you found the issue with using your spouse's SSN instead of yours! This is such a common mistake with joint returns. When you call the IRS tomorrow, make sure to have both your receipt from pay1040.com and your bank statement ready. Tell them specifically that the payment was made using your spouse's SSN but needs to be transferred to your account as the primary taxpayer. They should be able to locate the payment in their system and reapply it correctly to your return. Also mention the collection notice number from the letter you received - this will help them pull up your case quickly. Once they transfer the payment, ask them to send you a written confirmation and to remove any penalties that may have been assessed. You might also want to update your post with this resolution since it could help other people who run into the same issue. The SSN mix-up on joint returns seems to trip up a lot of folks!

This is such a helpful thread! I'm in a similar situation and have been going back and forth on this decision. One thing I wanted to add that might be useful - make sure to consider your long-term business goals when making this decision. If you're planning to eventually seek investors or potentially sell your business, having a Delaware or Nevada LLC might be more attractive to sophisticated investors who are familiar with those jurisdictions' business-friendly laws. Delaware in particular has a well-established court system for business disputes. However, if you're planning to stay a small, local business in Florida, the simplicity that Aiden mentioned probably makes the most sense. I've found that many entrepreneurs get caught up in optimizing for hypothetical future scenarios instead of focusing on what makes sense for their current situation. Also, don't forget that you can always domesticate (move) your LLC to a different state later if your needs change, though this does involve some paperwork and fees. It's not like you're locked into your initial choice forever. The privacy benefits are real, but as others have mentioned, if you're doing business locally, getting business licenses, or applying for loans, your information will likely become public through other channels anyway. Just something to keep in mind as you weigh the costs and benefits.

Great thread with lots of practical advice! As someone who works in tax compliance, I wanted to add a few technical points that might help: 1. **Nexus determination**: Physical presence isn't the only factor anymore. If you're actively managing your LLC from Florida (making business decisions, conducting operations, etc.), you almost certainly have nexus there regardless of where it's registered. 2. **Florida's "doing business" rules**: Florida requires foreign LLCs to register if they're "transacting business" in the state. This includes maintaining an office, owning/leasing property, or regularly conducting business activities - which sounds like your situation. 3. **Annual compliance costs**: Don't forget that maintaining good standing in multiple states means tracking different filing deadlines, registered agent requirements, and annual fees. Missing a filing in your formation state can cause your LLC to be dissolved, even if you're compliant in your operating state. 4. **Professional liability**: If you're in a profession that requires licensing (real estate, accounting, legal, etc.), some states have additional requirements for out-of-state business entities that can complicate things further. The privacy benefits are real, but for most small business owners, the administrative complexity and additional costs often aren't worth it unless you have specific asset protection concerns or are planning multi-state operations from the start. Florida's LLC laws are actually quite business-friendly, and you'd avoid the foreign registration requirements entirely.