I'm in the same boat but decided to go ahead and file without the donations this year. My donations only add up to about $750 in value, so it's only changing my refund by like $90. Not worth waiting weeks for that small amount when I'm getting back $3400 otherwise.

I've been dealing with this exact same frustration! After reading through all these comments, I ended up trying a hybrid approach. I used taxr.ai to organize all my donation receipts (which was honestly a lifesaver - had boxes of stuff from multiple charities), and then called the IRS using Claimyr to get an actual timeline. The IRS agent confirmed that Form 8283 should be available by January 28th, but she also mentioned something important - they're implementing new validation rules this year that might flag certain donations for review. She suggested keeping really detailed records of item conditions and fair market value calculations, especially for anything over $500. For anyone on the fence about waiting vs filing now, I'd say it depends on your donation amounts. I have about $2800 in donations which translates to roughly $400 in tax savings, so I'm waiting the extra week. But if you're only looking at $50-100 in tax benefits, probably not worth the hassle.

Ok so now I'm thoroughly confused! I have an LLC taxed as an S-corp... on the W-9, do I check LLC and write S, or do I just check S-Corp box??

This is such a common source of confusion! As someone who went through this exact same struggle when I first set up my LLC with S-Corp election, I totally understand the frustration. To clarify what others have said: if you formed an LLC (filed Articles of Organization with your state) and then elected S-Corporation tax treatment with the IRS (Form 2553), you are still legally an LLC. The S-Corp election only changes how the IRS taxes your business income - it doesn't change your actual business entity type. So on the W-9, you should: 1. Check the "Limited Liability Company" box 2. Write "S" on the line that asks for tax classification The "S-Corporation" checkbox is for businesses that were actually incorporated as corporations (filed Articles of Incorporation) and then elected S-Corp status. That's a different legal structure entirely. One tip: I always include a brief note on my W-9s that says something like "LLC electing S-Corp tax treatment per Form 2553" just to be extra clear. It helps avoid confusion with clients who might not understand the distinction and ensures the 1099s come back correctly.

This thread has been incredibly helpful! I'm dealing with a similar situation but with a twist - my settlement was from a workplace injury and included workers' comp benefits. From what I've researched, workers' comp is generally not taxable, but I'm confused because part of my settlement was for "future lost earnings capacity" rather than just medical expenses. Does anyone know if settlements for future earning capacity from workplace injuries follow the same tax-exempt rules as regular personal injury settlements? I'm worried this might be treated differently since it's more speculative than actual medical costs or current lost wages. Also seeing all the mentions of AI tools and IRS callback services - might have to try those since my situation seems pretty complex with multiple settlement components!

Reading through all these responses has been super helpful - I had no idea settlements could be so complicated tax-wise! It sounds like the key thing is figuring out exactly what each portion of the settlement was for. @Oliver Fischer - based on what others have shared, since your settlement was specifically for a car accident with physical injuries, the bulk of it (medical expenses, pain and suffering) should be tax-exempt. But you'll want to check if any portion was specifically designated for lost wages or other taxable categories. One thing I'd add that I don't think anyone mentioned yet - make sure to keep really detailed records of your settlement breakdown and any correspondence with the insurance company. Even if most of it isn't taxable, having clear documentation will be crucial if the IRS ever has questions later. I learned this lesson the hard way with a smaller settlement a few years back. The AI tools and IRS callback services people mentioned sound really promising for getting definitive answers on the tricky parts. Better to spend a little money upfront getting it right than dealing with potential audit issues down the road!

I just went through this exact scenario with my craft business! I purchased $3,750 in materials in December 2023 but didn't sell anything until January 2024. My accountant had me file a Schedule C showing zero income, and we listed the inventory on Part III but didn't claim it as COGS yet since nothing sold. We did deduct my $850 in legitimate business startup expenses like my LLC filing fee, website costs, and business cards. The inventory will become COGS when I file my 2024 taxes as items sell.

Thanks for all the helpful responses everyone! Just to clarify a few additional points that might help other newcomers in similar situations: Make sure you keep detailed records of your inventory purchases with receipts and invoices - the IRS will want to see documentation if questioned. Also, don't forget about the business use of home deduction if you're operating from your residence. Even with zero sales, you can still claim a portion of your home expenses if you have a dedicated business space. And regarding accounting methods - you typically need to choose cash vs accrual when you file your first Schedule C, so research which makes more sense for your business type before filing.

Has anyone else run into issues with lenders when taking this approach? I did something similar last year, and even though we technically kept the same borrowing entity (the LLC), the bank eventually found out about the ownership change and triggered a due-on-sale clause in the mortgage. Ended up having to refinance at a higher rate.

This is a complex situation that requires immediate attention to several tax and legal issues. First, yes, an S-Corp can legally own 100% of an LLC, but there are critical steps you need to take to properly structure this arrangement. Since you've acquired the single-member LLC, it will become a disregarded entity for federal tax purposes unless you make a specific election otherwise. This means all income, expenses, and activities of the LLC flow through to your S-Corp's tax return (Form 1120S). You'll need to file Form 8822-B to update the responsible party information with the IRS, changing it from the original owner's SSN to your S-Corp's EIN. Regarding your property tax avoidance strategy, I'd strongly recommend checking your local jurisdiction's rules immediately. Many counties and states have closed this "loophole" by defining transfers of controlling interest in entities as taxable events. You may still face reassessment despite purchasing the LLC rather than the property directly. For mortgage payments, you can continue making them through the LLC as normal, but be aware that many commercial loans contain change-of-control provisions that could trigger acceleration clauses when ownership changes occur. I'd recommend consulting with both a tax professional and attorney familiar with your jurisdiction's property tax laws to ensure you're compliant with all requirements and to address any potential issues before they become problems.