Just wanted to add one more tip that helped me when I had to paper file - make sure you're sending your return to the correct IRS processing center! The mailing address changes depending on your state and whether you're including a payment with your return. I almost sent mine to the wrong address because I used an old address I found online. The IRS website has a tool where you can enter your ZIP code to find the right mailing address. Also, consider using certified mail or at least getting a tracking number so you know your return arrived safely. Paper filing makes me nervous since there's no electronic confirmation like with e-filing!

As someone who's been through this exact situation, I can confirm what everyone else is saying - you definitely need Copy B, not Copy C. The labeling on the W-2 itself is your best guide: Copy B clearly states "To be filed with employee's federal tax return" while Copy C says "For employee's records." I'd recommend sending the whole printed sheet rather than trying to cut it perfectly. When I paper filed two years ago, I sent the entire page and had zero issues. The IRS processors are used to seeing W-2s in all different formats from various payroll systems. One thing I haven't seen mentioned yet - if you're really unsure about which copy your tax software was referring to, you might want to double-check the software's help documentation or contact their support. Sometimes there can be display errors or the software might be using outdated terminology. But based on official IRS guidance, Copy B is definitely what you need for your federal return. Also, don't forget to sign and date your return before mailing - that's an easy mistake that can delay processing!

Serious question - what happens if your friend just ignores the W-2G? Like the casino sent the form to the IRS, but if he has no other income and has been a non-filer for years, would the IRS really come after him for a small jackpot? Just wondering if it's even worth the hassle.

I went through something similar a few years ago. Had a decent casino win with a W-2G but was basically broke otherwise. The key thing to understand is that even though your friend has been a non-filer, that W-2G creates a filing requirement regardless of his other income. However, the good news is exactly what Sophia pointed out - if that $1600 is his only income for the year, it's well below the standard deduction threshold. He'll need to file a return to report it, but he won't actually owe any federal income tax. The IRS just needs to see that return to match against their records. I'd definitely recommend he files rather than ignoring it. The IRS matching system is pretty good at catching unreported gambling income, and it's much easier to file a simple return now than deal with notices and penalties later. Most free tax software can handle a basic return with just a W-2G.

One more thing to consider - the deadline for filing 1099s with the IRS is January 31, which is earlier than it used to be years ago. If this is your first time filing, don't get caught by surprise! Also, make sure you're collecting W-9 forms from vendors BEFORE you pay them, not scrambling to get them in January. I learned this the hard way when several of my vendors were impossible to reach when I needed their tax info.

This is such a common confusion for new S Corp owners! Your accountant is absolutely right about the 1099 requirement. I went through the exact same thing my first year and was shocked to learn about all the paperwork involved. One tip that really helped me: create a vendor tracking spreadsheet at the beginning of each tax year. Include columns for vendor name, business structure (sole prop, LLC, corp), total payments, and whether a W-9 is needed. Update it quarterly so you're not scrambling in January. Also, don't forget that the penalties for not filing required 1099s can be pretty steep - up to $280 per form if you're really late. The IRS has been cracking down on this more in recent years, so it's definitely worth getting compliant even if other people in your industry aren't doing it properly. Your colleague who says she's never had to issue them is probably either working with mostly incorporated vendors (who don't need 1099s) or simply not complying with the requirement. Better to be safe and follow your accountant's advice!

Great point about the home office deduction! This is something many people overlook. If you've claimed depreciation on any part of your home for business use, you'll need to "recapture" that depreciation when you sell - meaning you'll pay taxes on the amount you previously deducted, even if the rest of your gain qualifies for the exclusion. The recapture is taxed at a maximum rate of 25%, which can be a nasty surprise if you're not expecting it. Keep records of any home office deductions you've claimed over the years so you can calculate this correctly. Also worth noting - if you converted part of your home to rental property at any point (like renting out a basement apartment), similar rules apply. The IRS gets pretty strict about mixed-use properties when it comes to the primary residence exclusion.

Just wanted to add another perspective on documentation - I work as a tax preparer and see this situation frequently. Beyond organizing your receipts, consider creating a timeline document that shows the progression of improvements over the years. This helps if the IRS questions whether certain expenses were truly capital improvements versus repairs. For example, if you replaced a roof in 2010, that's clearly a capital improvement. But if you then had roof repairs in 2015, those would be maintenance expenses, not additional capital improvements. A chronological summary helps differentiate between the two and shows the logical progression of your home's improvements. Also, don't forget about permits! Many major improvements required building permits, and these are usually available from your local building department. Permit records can serve as excellent backup documentation, especially for older improvements where you might have lost receipts. They show the scope of work, dates, and often the estimated value of the improvement. One more tip: if you had any insurance claims for improvements (like upgrading electrical after a small fire), those insurance documents can also help establish the value and timing of capital improvements.

Just my two cents, but from experience - document EVERYTHING. Save your hotel receipts, take pictures of your work setup in the hotel, keep a log of hours worked, save emails sent from the hotel, etc. I had a similar deduction questioned once and having thorough documentation saved me.

This is a really interesting situation that I think more people deal with than they realize! I've been in a similar spot where my home office became unusable due to circumstances beyond my control (in my case, it was construction noise from next door that made client calls impossible). The consensus here is solid - you can likely deduct this as a legitimate business expense since your regular workspace is temporarily unavailable. What I'd add is to consider the "reasonable" test the IRS applies. A basic hotel room for a couple nights to maintain business operations? That sounds reasonable. A luxury suite at the Four Seasons? That might raise eyebrows. Also, keep track of your normal home office expenses during this period. You're not "double dipping" - you're replacing one workspace with another temporarily. Just make sure your documentation clearly shows this was a business necessity, not a personal preference to get away from the family (even though we all understand the need for quiet work time!). One last tip - if you have any client meetings or important calls scheduled during this time, document those as well. It shows the hotel expense was directly tied to maintaining your business operations.