I'm a Canadian freelance consultant who went through this exact same situation about 6 months ago! The confusion you're experiencing is totally normal - I got conflicting advice from multiple sources too. You absolutely should fill out the W-8BEN form. Here's what I learned after working through this with my tax advisor: The form isn't about whether YOU owe US taxes (you don't, since you're performing the work in Canada). It's about giving your US client the documentation they need to avoid withholding 30% of your payments and sending it to the IRS. Think of it this way - your Chicago client is legally required to withhold taxes from payments to foreign contractors UNLESS they have proper documentation showing you qualify for treaty benefits. The W-8BEN is that documentation. Without it, they'd have to: - Withhold 30% from every payment - Send that money to the IRS - Deal with additional paperwork and compliance headaches - Issue you a different tax form (1042-S instead of 1099) And you'd have to file a US tax return just to get your own money back - which could take months. For graphic design work, you'll cite Article XV of the US-Canada tax treaty. You can use your Canadian SIN (no US tax ID needed), and the form is valid for 3 years. Your client sent you this form because they know what they need for compliance. Completing it shows you're professional and understand cross-border requirements. Trust me, they'll appreciate having it on file rather than dealing with the withholding hassles!

I'm a Canadian freelance developer who's been working with US clients for over 4 years, and I want to echo what everyone else is saying - you absolutely need to complete the W-8BEN form! The confusion you're experiencing is super common. I remember getting similarly conflicting advice when I first started, including from IRS reps who weren't familiar with international contractor situations. Here's the bottom line: the W-8BEN isn't about YOUR tax obligations to the US (you won't owe any since you're working from Canada). It's entirely about protecting your client from having to withhold 30% of your payments and send that money to the IRS. Without the form, US tax law requires your Chicago client to do backup withholding, which creates a mess for both of you. They have to deal with extra paperwork and remittances, and you'd have to file a US tax return to get your own money back - a process that can take months. For graphic design work performed as an independent contractor, you'll want to cite Article XV (Independent Personal Services) of the US-Canada tax treaty. You can use your Canadian SIN - no need to get a US tax ID number. Your client sent you this form because they know what they need for compliance. Completing it is actually the professional thing to do and shows you understand cross-border business requirements. Don't worry about "causing problems" - you'd be causing way more problems by not providing the documentation they need! The form is straightforward and valid for 3 years once completed. Better to have it and not need it than need it and not have it.

One approach that worked well for my cousin and me was setting up an escrow account specifically for property taxes and other shared expenses. We each contribute our 50% share monthly (so about $283 each per month for your $6,800 annual tax bill). The account automatically pays the tax bill when due, and we both have access to statements showing exactly what each person contributed. This removes the stress of one person having to front the entire tax payment and wait for reimbursement. It also creates a clear paper trail for tax purposes since each person's contributions are documented. Most banks can set this up as a simple joint account with automatic transfers from your individual accounts. Just make sure the account agreement specifies that each person owns their contributions, not 50% of the total balance. The key is getting this arrangement documented in your co-ownership agreement so both the monthly contributions and the purpose of the account are legally clear. This way if your brother's income becomes unpredictable, you're not scrambling to cover his portion at tax time.

I'd recommend getting a formal partition agreement drafted by a real estate attorney. This is different from just a co-ownership agreement because it specifically addresses what happens if the co-ownership relationship breaks down. In your partition agreement, you can include the 50/50 tax responsibility, but also cover scenarios like what happens if your brother stops paying his share for multiple years. The partition agreement can establish that if one owner defaults on tax payments, the other owner can pay the full amount and then has the legal right to either: 1) Place a lien on the defaulting owner's share of the property, or 2) Force a sale of the property to recover the unpaid amounts. This gives you real legal recourse beyond just having a piece of paper saying he owes 50%. Michigan law is pretty favorable for this type of arrangement, and having it properly recorded with the county clerk gives you maximum protection. The upfront cost of getting this done right (probably $500-800 for a good attorney) is way less than what you could lose if things go sideways with your brother's finances down the road.

Last year when I used SBTPG, I got a text message when they received my refund and another one when they sent it to my bank. It took exactly 1 business day in between. I remember because I was obsessively checking my bank account every hour! The text came at 10:43am saying they'd received my refund, and then the next day around 2pm I got the second text saying it had been disbursed. My bank then took another day to make the funds available. So all in all it was about 2 business days from when the IRS sent it until I could actually use the money. Make sure you're signed up for text alerts if they offer them - made the waiting game much less stressful!

Thanks for asking this question! I'm in the exact same boat - filed through a different preparer this year and now dealing with SBTPG for the first time. Based on what everyone's sharing here, it sounds like 1-3 business days is pretty typical once they receive it from the IRS. I'm definitely going to check my pending transactions like Mateusius suggested - hadn't thought of that! Also going to sign up for those text alerts Caesar mentioned if they're available. It's reassuring to hear most people get their money pretty quickly, even if there's that extra middleman step we're not used to. Fingers crossed we both get our refunds soon for those business expenses!

This is such a helpful thread! I'm also a sole proprietor and had no idea about the difference between health insurance premiums (fully deductible) vs. other medical expenses (subject to the 7.5% AGI threshold). One thing I wanted to add - if you're planning to set up an HSA like several people mentioned, make sure your health plan is actually HSA-eligible first. It needs to be a qualified high-deductible health plan (HDHP). I made the mistake of assuming my high-deductible plan qualified, but it didn't meet all the IRS requirements and I had to pay penalties on contributions I'd already made. Also, for those considering the taxr.ai or similar services - I'd recommend at least getting a basic understanding of these rules yourself too. Even if you use a service, it helps to know enough to double-check their work. The IRS Publication 535 (Business Expenses) has a whole section on health insurance for self-employed folks that's actually pretty readable. Thanks everyone for sharing your experiences, especially about getting through to the IRS. That phone system is absolutely brutal!

As someone who just went through this exact situation last year, I can confirm what others have said about the health insurance premium deduction being huge for sole proprietors. The key thing that tripped me up initially was understanding that this deduction goes on Form 1040 Schedule 1 (line 17) as an "above the line" deduction, NOT on Schedule C with your other business expenses. This distinction matters because it reduces your adjusted gross income, which can help you qualify for other deductions and credits. It also reduces your self-employment tax base, which is an extra bonus. One practical tip: keep really good records of your premium payments throughout the year. I use a separate business checking account and make sure all health insurance payments come from there with clear descriptions. Makes tax prep so much easier and provides a clean audit trail if needed. Also worth noting - if you have a profitable year and are looking at a big tax bill, you might want to consider making your January premium payment in December to get the deduction in the current tax year. Just make sure you're actually liable for that payment before year-end!

Great question about Schedule E vs Schedule C! As others have mentioned, for rental properties (even in LLCs), you'll typically use Schedule E. The key distinction is that rental income is generally considered "passive income" rather than active business income. However, there's an important nuance many people miss: if you're actively involved in real estate as a business (like flipping houses, developing properties, or providing substantial services beyond normal landlord duties), then you might need Schedule C instead. For your situation with one rental property bringing in $1,750/month, Schedule E is definitely the right choice. Your $5,300 in repairs would go on Schedule E as well - just make sure to distinguish between repairs (deductible immediately) and improvements (depreciated over time). One tip: keep detailed records of all expenses separated by property if you plan to expand. It makes tax time much easier when you have multiple rentals. Also, don't forget about depreciation - it's often the biggest tax benefit rental property owners overlook!

This is such a common source of confusion for new rental property owners! You're definitely on the right track with Schedule E - that's correct for rental income from your single-member LLC. One thing I'd add to the great advice already given: since you mentioned spending $5,300 on repairs, make sure you understand which expenses are deductible in the year you pay them versus those that need to be depreciated. Also, don't forget about the depreciation deduction on the property itself - this is often one of the biggest tax benefits of rental real estate that new investors miss. The IRS connection between your LLC's EIN and your SSN happens automatically when you apply for the EIN, so you don't need to worry about that. Just make sure to keep good records of income and expenses separated by property if you plan to expand your portfolio later. Also, consider setting up a separate business bank account for your LLC if you haven't already. While it's not required for tax purposes, it makes record-keeping much cleaner and helps maintain the corporate veil for liability protection. Good luck with your rental property journey!