Just wanted to add my experience here - I had the exact same Wealthfront/FreeTaxUSA struggle last year! What finally worked for me was logging into my Wealthfront account and downloading ALL the tax documents, not just the main 1099-DIV. There's usually a "Tax Center" or "Tax Documents" section where you can find the supplemental state information that breaks down which dividends are exempt by state. Once I had that state breakdown, entering it in FreeTaxUSA was actually straightforward. In the state section (after you've entered your federal 1099-DIV info), there's a specific question about state-exempt interest and dividends. You just enter the amount that's exempt for your specific state based on that Wealthfront supplemental document. The key thing I learned is that you can't rely on just the 1099-DIV form - you really need that additional state-by-state breakdown that Wealthfront provides separately. Hope this helps save you some of the hair-pulling I went through!

This thread has been incredibly helpful! I was in the exact same boat with Wealthfront and FreeTaxUSA. After reading through everyone's experiences, I found the supplemental tax documents in my Wealthfront Tax Center (thanks @Dmitry!) and was able to locate the state-exempt dividend amounts. For anyone else struggling with this: the key is definitely getting ALL the tax documents from Wealthfront, not just the 1099-DIV. The "State Tax Supplement" document shows exactly which portions of your dividends are exempt from state taxes by state. Then in FreeTaxUSA, after you enter your 1099-DIV in the federal section, you go to your state return and look for the section about exempt interest and dividends - that's where you enter the state-exempt amounts from the supplement. It's actually pretty straightforward once you have all the right documents, but Wealthfront could definitely make this clearer for first-time users. Hope this saves someone else the headache I went through!

Don't forget that as a college student, you might qualify for education tax credits like the American Opportunity Credit or the Lifetime Learning Credit! Those can be worth up to $2,500 depending on your situation. So definitely file that W-2 and claim your education expenses too!

Just wanted to chime in as someone who was in almost the exact same situation last year! I had a campus job that lasted only a month and made about $520, and I was so confused about whether to report it since it seemed like such a tiny amount. The advice here is spot on - you absolutely need to report ALL W-2 income, no matter how small. I learned this the hard way when I initially didn't include mine and got a notice from the IRS a few months later asking about the discrepancy. It wasn't a huge deal to fix, but it was definitely stressful and could have been avoided. One thing that really helped me was keeping track of ALL my tax documents in one place - even the small ones. Now I have a simple folder (physical and digital) where everything goes as soon as I receive it. Makes filing so much easier when you're not scrambling to find that one random W-2 from a job you barely remember! Also, definitely look into those education credits Oliver mentioned - they can make a huge difference for students. Good luck with your first time filing!

Has anyone tried using the relatively new safe harbor for rental real estate under Section 199A? It might not solve the passive activity loss issue directly, but it could provide a qualified business income deduction that offsets some of the S-Corp income.

Another consideration for your grouping election - make sure you're prepared to defend the "appropriate economic unit" determination if the IRS challenges it. The regulations under 469(c)(7)(A) list five factors they consider: similarities and differences in types of business, extent of common control, geographical location, interdependencies between activities, and extent of common ownership. In your case, you have strong arguments for several factors: common control (you own 100% of both), geographical location (same property), and interdependence (the S-Corp depends on the real estate for its operations). The fact that your S-Corp is the primary tenant actually strengthens the interdependence argument. One tip: when you file the grouping statement with your return, be very specific about which factors you're relying on and provide concrete details. Don't just say "common control and geographical location" - explain that you have 100% ownership of both entities and that the S-Corp operates exclusively from the LLC-owned property under a triple-net lease arrangement. Also keep detailed records of your material participation in both activities. The IRS may scrutinize whether you're truly materially participating in the rental activity or if it's just passive ownership.

Thanks for sharing all these perspectives! As someone who's been dealing with payroll compliance for years, I want to emphasize that proper W-2 reporting really is the safest approach here. Nick, for your $65/month benefit, you're looking at adding about $780 annually to each employee's taxable income. While that might seem like a lot, many employees still find significant value in employer-sponsored gym benefits even when taxable - especially if you can negotiate group rates that are better than what they'd pay individually. One approach I've seen work well is being completely transparent about the tax implications upfront, but also highlighting the total value they're receiving. For example, if you can get gym memberships that would normally cost $80/month for $65 through group purchasing power, employees are still getting a $15/month discount even after paying taxes on the benefit. The key is clear communication - don't let it be a surprise on their first W-2. Include the tax impact in your initial rollout materials so employees can make informed decisions about participation.

I've been working in benefits administration for about 8 years and wanted to add a few practical tips that might help with implementation. First, regarding group rates - absolutely pursue this! I've seen companies get 15-25% discounts with major chains like LA Fitness, Planet Fitness, and regional gym networks when you can guarantee a certain number of memberships (usually 20+ employees). Some gyms will even waive enrollment fees entirely for corporate programs. For communication, I always recommend a "total compensation" approach. Create a simple one-page breakdown showing: - Monthly gym benefit: $65 - Employee tax impact (assuming 22% bracket): ~$14 - Net monthly value to employee: $51 - Compared to individual membership cost: $80 - Total monthly savings: $29 Also consider offering it as an opt-in benefit during open enrollment rather than automatic enrollment. This way employees who are already paying for gym memberships can see the clear savings, while those who aren't interested don't feel like they're getting a "tax increase." One more tip - if you have any employees with HSAs, remind them that they might be able to use HSA funds for gym memberships if they have a letter of medical necessity from their doctor. This can help offset the tax impact for some employees.

Wait I'm confused... is it actually better to pay the tax and file for a refund so you can go straight to district court instead of tax court? I have a case where IRS disallowed some charitable contributions (about $13k in deductions) and I'm trying to figure out the best court to take this to.

Just to add another perspective here - I went through this exact situation last year with a business expense dispute. Lost in Tax Court and was devastated thinking I had no options left. What I learned is that while you can't start fresh in district court for the same tax issue, your appeal to the Circuit Court of Appeals is actually a really important opportunity. The appellate courts sometimes reverse Tax Court decisions, especially on questions of law rather than fact. My attorney explained that Tax Court judges are very experienced with tax law but sometimes the Circuit Courts take a broader view of statutory interpretation. We appealed my case to the 9th Circuit and while we didn't win completely, we got a partial reversal that saved me about $15,000. Don't give up after Tax Court - the appeals process exists for a reason and it's often your best (and only) path forward after losing there.