Great thread with lots of helpful insights! I went through this exact situation with my Aetna disability payments earlier this year. One thing I'd add is to check if your employer continues any benefits during your disability leave that might affect your tax situation. In my case, my company continued paying their portion of my health insurance premiums, which meant I had less taxable income than I initially calculated. This actually reduced the amount I needed to have withheld. I had to adjust my W-4S form mid-way through my leave to avoid over-withholding. Also, if you're planning to return to work part-way through the tax year, remember that your regular paycheck withholding will resume, so you don't want to double up and have too much withheld overall. I used a simple spreadsheet to track my total projected income and withholding across both my disability payments and expected regular paychecks for the remainder of the year. The key is looking at your total annual tax picture, not just the disability payment period in isolation.

This is such a helpful discussion! I'm dealing with a similar W-4S situation right now with my Aflac disability coverage. One thing I learned from my tax preparer that might be useful - if you're married filing jointly, make sure to consider your spouse's income and withholding when determining your disability withholding rate. In my case, my spouse's regular paycheck withholding was already covering a good portion of our combined tax liability, so I didn't need to withhold as much from my disability payments as I initially thought. We calculated that withholding about 15% from my disability pay (compared to the 22% from my regular paychecks) would keep us on track. Also, don't forget that if you're paying for your own disability insurance premiums with after-tax dollars, those payments are generally not taxable when you receive them. But if your employer pays the premiums (which sounds like your case with MetLife), then the benefits are taxable. This distinction can significantly impact how much you need to withhold.

Just finished dealing with this. I found the most confusing part was column C in Schedule A Part 1 where you have to list donor's adjusted basis. For real estate that's appreciated a lot, this number can be WAY different from the FMV you're reporting. Make sure you have good records of what you originally paid + any capital improvements. Without that you're just guessing at your basis which could cause problems later. Also heads up - you might need to file a state gift tax return too depending on where you live. I had to file in Connecticut and that was a whole separate headache.

I went through a similar nightmare with Form 709 last year! One thing that really helped me was creating a simple spreadsheet to track everything before filling out the actual form. I made columns for: property description, full FMV, my basis, spouse's portion, and my portion. For the split gift reporting, remember that even though you're each filing separate 709s, the gift splitting election applies to ALL gifts made during the tax year by either spouse - not just this one property. So if either of you made any other gifts during the year (even small ones), those need to be reported consistently with the splitting election. Also, double-check that you're using the correct annual exclusion amounts. For 2024, it's $18,000 per recipient ($36,000 if splitting), but make sure you're using the right year's limits for when the gift was actually made. The deadline stress is real, but you've got this! The IRS is generally reasonable about gift tax issues if you make a good faith effort to comply.

Paolo, you've gotten some excellent advice here! I just completed my single member LLC setup a few months ago and went through the exact same confusion on Form SS-4. Yes, "Sole Proprietor" is absolutely the correct selection for line 9a - I know it feels weird since you just formed an LLC, but that's how the IRS wants it done. The key thing to understand is that your LLC gives you liability protection at the state level, while the federal tax treatment is completely separate. By default, the IRS treats single-member LLCs as "disregarded entities," which means you get taxed like a sole proprietor even though you have the legal protections of an LLC. It's actually the best of both worlds for most new businesses. Regarding the S-Corp election your friends mentioned - that's something they did AFTER getting their EIN by filing Form 2553. You don't need to worry about that on your initial SS-4 form. Most businesses don't benefit from S-Corp treatment until they're generating significant profit (usually $40K+ annually) because of the additional payroll and administrative costs involved. My recommendation: select "Sole Proprietor," get your EIN, open a business bank account, and focus on growing your business. You can always explore more complex tax elections later when your income justifies it. Don't overthink this initial step - you're making the right choice!

Paolo, you're definitely making the right choice! I just went through this exact same process with my single member LLC about 4 months ago and had the exact same confusion on Form SS-4. Yes, you should absolutely select "Sole Proprietor" on line 9a. I know it feels counterintuitive since you just formed an LLC, but the IRS treats single-member LLCs as "disregarded entities" by default. This means you get the liability protection of the LLC structure while being taxed as a sole proprietor - honestly, it's the perfect setup for most new businesses. Your friends with LLCs taxed as S-Corps made that election AFTER getting their EIN by filing Form 2553. That's a completely separate process you can explore later if your business income grows enough to justify the additional complexity (usually around $50K+ in annual profit when the self-employment tax savings outweigh the extra administrative costs). Don't stress about getting everything perfect right now. Select "Sole Proprietor," get your EIN, and focus on actually building your business. You can always make more complex tax elections down the road when you have real income to optimize. The most important thing is just getting started - you're not locked into this choice forever!

As a newcomer to nonprofit management, I've been following this discussion closely and it's been incredibly educational! Our youth hockey organization is in a similar situation - we've received some generous donations and want to help families with tournament travel costs, but our board has been nervous about potential IRS issues. Reading through all these responses has given me so much confidence that this is not only allowed but actually a great use of our charitable funds. The key takeaways I'm getting are: establish clear written policies, use objective criteria for determining need (like the 200% poverty level guideline), document everything thoroughly, and make sure assistance is available across all our programs equally. I especially appreciate the suggestion to frame this as a scholarship program for youth development rather than just financial assistance - that really clarifies the charitable purpose. The idea of setting aside a specific percentage of our annual budget (rather than just using "extra" donations) also makes this feel more intentional and sustainable. One thing I'm curious about - for organizations just starting this type of program, is it better to pilot with a small group first to work out the kinks, or should we establish the full policy framework upfront and launch comprehensively? We have about 150 families across different age groups and skill levels, so the scope could get pretty large pretty quickly. Thanks to everyone who shared their experiences - this thread has been invaluable for helping us think through how to structure this properly!

This is such a timely discussion! As someone new to nonprofit governance, I've been researching this exact question for our youth swimming program. After reading through all these excellent responses, I'm convinced this is not only permissible but actually represents the best kind of charitable programming - directly advancing your mission while serving families who need support. One aspect I haven't seen mentioned yet is the potential tax implications for the families receiving assistance. From what I've researched, travel assistance provided by a 501(c)(3) for program-related activities typically isn't considered taxable income to the recipients, since it's directly tied to your charitable purpose rather than being a personal benefit. However, it's worth confirming this with your accountant, especially for larger assistance amounts. I'm also impressed by how many organizations have successfully implemented similar programs. It really reinforces that this isn't some edge case or gray area - it's a legitimate and common way for youth sports nonprofits to fulfill their charitable missions. The consistency in advice about clear policies, objective criteria, and proper documentation shows there's a well-established framework to follow. Your mission statement language is perfect justification, and the enthusiasm from your board is a great foundation. With proper policies in place, this could become one of your most impactful programs!

I went through a similar situation with our community tennis facility a few years ago. The key issue we faced was proving that our primary purpose was charitable rather than recreational. What really helped us was documenting everything - we created detailed records showing how much time, resources, and revenue was dedicated to our charitable programs versus general operations. The IRS wants to see that charitable activities aren't just a side benefit but are central to your mission. For your golf course, I'd suggest quantifying your community impact: How many kids participate in your youth programs? What's your scholarship program like? Do you offer free or reduced-rate access for seniors, veterans, or low-income families? The more you can demonstrate measurable community benefit, the stronger your 501(c)(3) case becomes. Also, make sure your articles of incorporation and bylaws explicitly state your charitable purposes using IRS-approved language. We had to amend ours to be more specific about our educational and charitable objectives rather than just saying we "serve the community.

As someone who works in nonprofit compliance, I'd recommend getting professional help with your IRS application. Golf courses face unique challenges for 501(c)(3) status because the IRS scrutinizes recreational facilities heavily. The biggest hurdle you'll face is the "private benefit" test - if your course primarily serves golfers who can afford green fees rather than truly serving charitable purposes, the IRS will likely deny your application. You need to demonstrate that charitable activities are your primary purpose, not just a secondary benefit. Consider this approach: restructure your programs so that at least 60-70% of your course time and resources support clearly charitable activities. This might mean dedicating specific days/times exclusively to youth programs, adaptive golf for disabled individuals, or veteran therapy programs. Document everything with participant numbers, volunteer hours, and measurable community impact. Also review your bylaws carefully - they need to include specific "charitable purposes" language and dissolution clauses that meet IRS requirements. Many state nonprofits fail federal review because their governing documents don't align with federal standards. The separate foundation approach others mentioned is actually quite common and might be your best bet if restructuring the main operation isn't feasible. This lets you maintain normal golf operations while creating a clear charitable arm for grants and tax-deductible donations.