Has anyone dealt with this for an installment sale? I'm selling my rental property with owner financing (buyer paying me over 10 years), and I'm confused about how the bulk sales withholding works in this case. Do they withhold from each payment I receive or just the down payment?

Just wanted to add something that might help others - timing is crucial with bulk sales withholding exemptions. I learned this the hard way when selling my duplex in Illinois last year. Most states require you to submit exemption applications 10-30 days before your scheduled closing date. I waited until 5 days before closing to apply and my exemption was still being processed when we were supposed to close. We had to delay the closing by two weeks, which cost me extra carrying costs and almost killed the deal when the buyer got frustrated. The lesson: start the exemption process as soon as you have a signed purchase agreement, not when you're getting close to closing. Even if you think you might not qualify for an exemption, it's worth applying early because the worst case is they deny it and you're back to the standard withholding anyway. Also, some states have emergency or expedited processing for exemptions if you're close to closing, but they usually charge extra fees (mine was $150 for expedited processing in Illinois). Much better to plan ahead!

Just to share my experience - I run a Mexican manufacturing company that sells products to US distributors. We file both forms every year. The 1120-F reports our US-connected income (even though we claim it's exempt under the treaty), and the F8833 specifically details which treaty articles we're relying on. Our tax advisor said the 1120-F is mandatory regardless of treaty benefits, while F8833 is what actually substantiates our treaty position. Last year we almost didn't file F8833 thinking it was unnecessary paperwork, but then learned about the $10,000 penalty. Not worth the risk!

As someone who's dealt with similar international tax complexities, I want to emphasize the importance of getting this right from the start. The interaction between Forms 1120-F and 8833 can be tricky, especially when you're trying to claim treaty benefits. From my experience with foreign corporations doing business with US clients, here's what I've learned: even if you believe you're fully exempt under the Singapore-US treaty, filing both forms creates a clear paper trail that demonstrates compliance and good faith. The 1120-F establishes your filing history and starts the statute of limitations clock, while the 8833 provides the specific legal justification for your treaty position. One thing to watch out for - make sure you understand the "permanent establishment" rules under the current treaty. With digital services and remote work becoming more common, the definition of what constitutes a PE has been evolving. If any of your consulting work involves ongoing projects or regular clients, you'll want to carefully analyze whether this creates a taxable presence in the US. I'd strongly recommend getting professional guidance for at least your first filing to establish the correct approach, then you might be able to handle subsequent years yourself once the pattern is established.

Quick tip: Download the Stride app to track your mileage automatically. I drive for multiple apps and it's been a lifesaver. Just hit "start work" when you begin and "end work" when you're done. At tax time, it gives you a report with all your business miles and the deduction amount.

I totally understand the frustration! I went through the same confusion with my gig work taxes last year. Here's what I learned that might help: Your W-2 income and 1099 gig work are reported separately - don't try to combine them. The W-2 goes on the main 1040 form, and your gig income goes on Schedule C where you can deduct your business expenses. For your mileage, you're on the right track! You can deduct either actual vehicle expenses OR the standard mileage rate (currently $0.655 per mile for 2023). Since you tracked 15,600 miles, that's about $10,218 in deductions, which is substantial. Don't stress too much about making mistakes - the IRS typically sends letters first if there are issues, not immediate bank account seizures. They actually want to help you get it right. One thing that saved me: keep detailed records of everything. Besides mileage, you might be able to deduct things like phone bills (business portion), car washes, parking fees, and even some supplies. The key is having documentation. Have you considered using tax software specifically designed for gig workers? It can walk you through Schedule C step-by-step and make sure you don't miss any deductions. Much less stressful than trying to figure out the forms manually!

Just a heads up - if you use payment apps like Venmo, PayPal, Cash App, etc. to receive payments, new rules require them to send 1099-K forms if you receive over $5,000 in a calendar year. This was supposed to be $600 but they increased the threshold again. Keep track of these payments yourself rather than relying on the apps to report correctly!

Great advice from everyone here! One additional thing to consider - since you're dealing with potentially sensitive content, you might want to think about business structure down the road. While you can definitely start as a sole proprietor (which is what you are by default), if your income grows significantly, you might want to consider forming an LLC for liability protection and potential tax benefits. Also, make sure you're keeping digital copies of ALL your records - income receipts, expense receipts, bank statements showing business transactions, etc. The IRS can audit up to 3 years back (longer in some cases), so having organized digital records will save you major headaches if that ever happens. I use a simple spreadsheet but there are also apps like QuickBooks Self-Employed that can help track everything automatically by linking to your bank accounts and categorizing transactions. One last tip: set aside 25-30% of your income in a separate savings account for taxes. This covers both income tax and self-employment tax. It's better to save too much and get a refund than to owe money you don't have come tax time!

Don't forget about foreign stocks if your dad had any! My mother inherited some Canadian company stocks from my father, and there were special rules about foreign securities that almost caused us to miss out on significant tax advantages. The step-up basis applies, but there can be currency conversion considerations too. The broker should be handling this, but it's worth specifically asking how they're determining the stepped-up basis for any foreign investments. In our case, they initially only adjusted for the stock price change but missed the currency fluctuation component.

I'm sorry for your loss, Aisha. Going through this process while grieving is incredibly difficult, and I can relate to feeling overwhelmed by all the financial details. One thing I haven't seen mentioned yet is the importance of getting multiple copies of the death certificate from the funeral home or vital records office. Each brokerage will likely want an original or certified copy, and if your father had accounts at several firms, you'll need quite a few. I learned this the hard way when we had to wait weeks for additional copies while the estate settlement was delayed. Also, keep detailed records of everything - dates you contacted each brokerage, names of representatives you spoke with, and any reference numbers they give you. Some brokerages are much faster at processing these requests than others, and having good documentation helps if you need to follow up or if there are any discrepancies later. The step-up basis will definitely help reduce future tax burdens when your mom eventually sells any of these investments, so it's worth taking the time to get it done properly. Wishing you and your family the best as you navigate this difficult time.