One thing nobody's mentioned yet is the QBI (Qualified Business Income) deduction. With both an LLC and S corp, you potentially get a 20% deduction on your business income, but the calculation is different. For a single-member LLC, the QBI deduction applies to your net profit after the self-employment tax deduction. With an S corp, it applies to your business profit minus your salary. So when you're comparing tax savings, make sure you factor this in too! I switched from LLC to S corp last year and saved on self-employment taxes, but my QBI deduction was slightly lower. Still came out ahead overall though.

Dont forget state taxes! Some states tax S corps differently than LLCs. California, for example, has a minimum $800 tax for S corps PLUS a 1.5% tax on net income. I learned this the hard way - saved about $4k in federal taxes by switching to an S corp, then got hit with $2,200 in additional CA taxes I wasn't expecting. Still came out ahead but not by as much as I thought.

22 Does anyone know if electric vehicles get any special depreciation treatment for business use? I'm looking at a Tesla Model Y which is around 4,500 lbs (so under the 6,000 threshold) but heard there might be extra incentives.

Just wanted to share my experience as someone who recently went through this exact decision! I ended up choosing the heavier vehicle (Ford F-150 at 6,100 lbs) over a smaller SUV, and it made a huge difference on my taxes. The key thing I learned is that you need to look at your total business use percentage and cash flow needs. Even though the heavier truck cost me $12,000 more upfront, the enhanced depreciation benefits meant I could deduct about $25,000 more in year one (at 80% business use). This significantly reduced my tax liability and improved my cash flow. One tip - make sure you get the GVWR (Gross Vehicle Weight Rating) from the manufacturer's specs, not the curb weight. The GVWR is what the IRS uses to determine eligibility. Some vehicles that seem close to 6,000 lbs might actually qualify based on their GVWR even if their curb weight is lower. Also, don't forget to factor in your state taxes too - some states have additional depreciation benefits for business vehicles that can make the decision even more favorable toward the heavier option.

Make sure to double check your state tax return too! I had the exact same issue with inherited stocks last year. Got my federal return sorted out with the lower capital gains rate, but completely missed that my state was still taxing the gains as regular income. Most states follow federal rules for capital gains, but some have their own calculations.

Just want to add one more thing that might help others dealing with inherited investments - make sure you understand the "stepped-up basis" rules too. When you inherit stocks, the cost basis is "stepped up" to the fair market value on the date of death, which means you only pay capital gains tax on appreciation that happens after you inherited them. This is different from if someone had gifted you the stocks while alive (where you'd use their original cost basis). The K1 you received should already reflect this stepped-up basis, but it's worth understanding so you can verify the numbers look correct. Also, if the estate held the stocks for more than a year before distributing them to you, they automatically qualify for long-term capital gains treatment regardless of how long you personally held them. This is another inheritance tax benefit that many people don't realize exists.

Has anyone actually tried just putting "0" (zero) in Box 6 on TurboTax to see if that works? I'm facing the same issue and wondering if that's a valid workaround.

I had this exact same problem last year! TurboTax was being super finicky about Box 6 even though my 1099-NEC had it completely blank. After trying several approaches, I found that entering just the two-letter state code where the withholding occurred worked perfectly. In your case, since you mentioned having state tax withheld in Box 5, try entering "PA" (assuming that's where the withholding went based on your earlier comment). This satisfies TurboTax's requirement without making up fake information, and it's actually the logical solution since state withholding has to correspond to some state. I was worried about doing this at first, but my return was processed without any issues and I never heard anything from the IRS or state about it. The key thing is that you're accurately reporting your income and the actual withholding amounts - the state identifier is really just for their matching systems.

Just so you know, you might want to look at alternatives to TurboTax too. I used H&R Block Premium last year for a very similar situation (3 rental properties, side business, backdoor Roth) and found it handled everything well for a lower price than TurboTax Self-Employed.

Based on your complex tax situation, you definitely need TurboTax Self-Employed. Here's why: Your rental properties in multiple states require multi-state tax filing capabilities that only Premier/Self-Employed versions handle well. The Self-Employed version is better for this since you also have 1099 consulting income. For your Canadian accounts ($80k CAD retirement + $35k CAD checking/savings = $115k CAD total), you'll need to file FBAR (FinCEN Form 114) since you exceed the $10,000 USD threshold. Self-Employed includes guidance for these foreign account reporting requirements. The backdoor Roth IRAs (both regular and mega) require careful Form 8606 reporting to avoid double taxation, and Self-Employed has better guidance for these transactions. Your Airbnb STR situation using the 14-day rule needs proper reporting to avoid audit flags - Self-Employed handles short-term rental income better than lower tiers. The consulting work from home likely qualifies for home office deductions, which Self-Employed specializes in calculating correctly. Given all these moving parts (multiple income streams, multi-state rentals, foreign accounts, complex retirement contributions), the Self-Employed version will save you more in properly claimed deductions than the extra cost over Premier. The specialized guidance alone is worth it for your situation.