Have you considered whether you might qualify for the Head of Household filing status? It could make a significant difference with three dependents. Also, did you receive any advance Child Tax Credit payments during 2023? Those would need to be reconciled on your return. What about educational expenses for any of your dependents? The American Opportunity Credit or Lifetime Learning Credit might apply.

With $65k and 3 dependents, you might actually be surprised by your tax situation! The Child Tax Credit alone could give you up to $6,000 in credits ($2,000 per qualifying child under 17). Plus, if you're filing as Head of Household, your standard deduction is $20,800 for 2023, which is significantly higher than single filers. A few quick questions that could help your situation: - Are you maxing out any pre-tax retirement contributions? You still have until April 15th to contribute to a Traditional IRA - Did you have proper withholding all year, or did something change mid-year? - Are you paying for childcare? The Child and Dependent Care Credit could provide additional savings Don't panic yet - run through a tax calculator or software to get a clearer picture. You might be in much better shape than you think!

This is a really complex area where getting it wrong can be extremely costly. From what I understand, the IRS has been pretty strict about the "substantially all" requirement for QSBS eligibility. One thing that might be worth exploring is whether there are any recent private letter rulings or tax court cases that have addressed similar fact patterns. The tax code is one thing, but how the IRS actually interprets and applies these rules in practice can sometimes be different. Also, have you considered the potential impact of the Tax Cuts and Jobs Act changes? Some of the QSBS provisions were affected, and there might be transition rules that could impact your timing strategy. I'd strongly recommend getting a formal tax opinion from a law firm that specializes in this area before making any final decisions. The potential tax savings from QSBS (up to $10M or 10x basis exclusion) are significant enough that it's worth paying for expert advice upfront rather than discovering problems later.

This thread has covered the key issues really well. I'd just add one practical consideration that hasn't been mentioned - the compliance burden of switching tax elections mid-stream. When you elect S-Corp status and then revoke it later, there are specific forms and timing requirements that can trip you up. Form 1120S needs to be filed during S-Corp years, then you switch back to Form 1120 for C-Corp status. Missing deadlines or filing incorrectly during these transitions can create additional problems beyond just the QSBS eligibility issues. Also, if you have multiple shareholders, the S-Corp election requires unanimous consent, and revoking it later requires majority consent. This can get complicated if your shareholder base changes over those 4-5 years. Given all the complexity and the fact that you'd lose QSBS eligibility anyway, starting as a C-Corp from day one really does seem like the cleaner approach, especially if you're confident about meeting the other QSBS requirements.

One practical consideration that might help with your GP/LP decision: look at who will actually be managing the property day-to-day. The IRS generally expects the GP to have meaningful involvement in operations, so if one of you is naturally going to handle tenant relations, maintenance coordination, and financial management, they're probably the better choice for GP. Also, since you mentioned this is a 50-50 split between siblings, make sure your partnership agreement clearly spells out decision-making procedures for major decisions like capital improvements, tenant selection, and eventual sale. Even with one GP, you'll want to define what requires unanimous consent versus what the GP can decide independently. For a $425K property generating $3,200/month, the self-employment tax difference between GP and LP could be around $4,000-5,000 annually (roughly 15.3% of half the net rental income), so factor that into your decision alongside the liability and control considerations others have mentioned.

One thing I haven't seen mentioned yet is the impact of passive activity loss rules on your partnership structure. Since rental real estate is generally considered a passive activity for tax purposes, any losses from the property might be limited in how they can offset other income. However, if one partner qualifies as a "real estate professional" under IRS rules (which requires 750+ hours annually in real estate activities and more than half of their personal services), they might be able to treat rental losses as non-passive. This could be a significant factor in deciding who should be the GP, especially if one of you works in real estate or property management. Also, consider looking into cost segregation studies for a property of that value. With a $425K rental property, you might be able to accelerate depreciation on certain components (flooring, fixtures, landscaping) which could create substantial tax benefits in the early years. The GP typically makes these kinds of tax elections, so factor that decision-making authority into who you want in that role. Given the monthly income you're expecting, make sure you're also planning for quarterly estimated tax payments. The GP will need to factor in both regular income tax and self-employment tax when calculating these payments.

If anyone is still following this thread, I just wanted to add that I had a similar issue with TaxAct (not FreeTaxUSA) and RIC foreign income. The solution for me was to make sure I entered the correct country codes for each foreign tax paid rather than using "various" as the country. Once I did that, e-filing worked fine. Maybe try that approach in FreeTaxUSA too? Sometimes these tax software issues have simple workarounds if you get the right guidance.

I just went through this exact same nightmare with FreeTaxUSA and RIC foreign income from my mutual fund investments. After reading through all these suggestions, I want to share what finally worked for me. The key was getting the Form 1116 allocations exactly right. I had foreign income from three different countries through my Vanguard international fund, and FreeTaxUSA kept rejecting my e-file because I was lumping everything together. Here's what I had to do: 1. Separate each country's foreign taxes paid into individual entries rather than using "Various" or combining them 2. Make sure the passive income category was selected correctly for each foreign source 3. Double-check that the foreign tax credit amounts matched exactly with what was on my 1099-DIV The whole process was incredibly frustrating because FreeTaxUSA's error messages were completely unhelpful - they just said "foreign income not supported for e-filing" without explaining what specifically was wrong. But once I got the allocations right, it went through immediately. For anyone still struggling with this, don't give up on FreeTaxUSA if you've already entered everything. The software CAN handle RIC foreign income for e-filing, it's just very picky about how you enter the information.

I went through this exact same situation last year as a University of Alberta student who did an internship in Boston! The Sprintax university issue is super frustrating - I ended up having to abandon it entirely. What worked for me was using FreeTaxUSA's non-resident option. It's much more flexible about international students and doesn't get hung up on the university selection. You can manually enter your Canadian school info without any problems. The interface walks you through the 1040NR pretty clearly, and it automatically applies the US-Canada tax treaty benefits when you indicate you're a Canadian resident. One tip: make sure you have your Social Insurance Number (SIN) from Canada handy, as some forms ask for your home country tax ID. Also, if you made under $12,950 (which you did at $12K), you might not owe any federal taxes anyway, but you'll still want to file to get back whatever was withheld from your paychecks. The whole process took me about 2 hours once I found the right software, versus the days I wasted fighting with Sprintax. Good luck!

I'm in almost the exact same boat! Canadian student at UBC who did a software internship in San Francisco last summer. The Sprintax university issue drove me absolutely crazy - spent hours trying to find a workaround before giving up. I ended up using TurboTax's non-resident filing option, which was much more flexible. It has a section for "other" educational institutions where you can manually enter your Canadian university details without any validation issues. The software automatically detected that I qualified for treaty benefits and walked me through claiming them properly. One thing that really helped was calling my internship company's payroll department directly. They were able to confirm exactly how much was withheld and whether they had applied any treaty benefits during the year. Turns out they hadn't applied the full treaty reduction, so I got back almost $1,800 between federal and California state refunds. Also, make sure you keep track of any state taxes you pay - you can claim those as foreign tax credits when you file your Canadian return next year. The whole dual-country filing process is a pain, but the refunds usually make it worth the hassle!