Has anyone used Gusto for both payroll AND S-Corp compliance help? Their website says they offer S-Corp services but im not sure if that's enough or if I still need a separate tax person?

You're definitely not too late for 2024! The March 15th deadline mentioned earlier is for existing businesses, but if you're converting from an LLC to S-Corp election, you have different options. You can file Form 2553 and request late election relief if you missed the standard deadline - the IRS is pretty reasonable about this for valid business reasons. Given your $140k profit, the tax savings will be substantial. You're looking at saving around $9,800 in self-employment taxes annually (assuming you set a reasonable salary around $70k). For your existing setup, you're already ahead of most people - Gusto handles payroll perfectly for S-Corps, and Wave will work fine for bookkeeping. The main additions you'll need are: - Quarterly 941 payroll tax returns (Gusto can handle these) - Annual 1120-S business return - Reasonable salary documentation - More careful expense tracking I'd recommend finding a CPA who specializes in S-Corps for the initial setup and annual filing. You don't need monthly CPA services - quarterly check-ins during your first year should be sufficient. Look for someone who can help justify your salary choice and ensure you're maximizing the tax benefits. The complexity increase is manageable, especially with your existing systems in place. The tax savings alone will more than cover the additional professional fees.

Don't forget about the wash sale rule if you're trying to do tax loss harvesting! If you sell investments at a loss and buy "substantially identical" securities within 30 days before or after the sale, you can't claim the loss for tax purposes.

Great question about ESPP gains and tax loss harvesting! Yes, you can definitely use your regular brokerage losses to offset ESPP capital gains - the IRS treats all capital gains and losses the same regardless of source. However, make sure you're calculating your ESPP gains correctly. With a 15% discount and immediate sale after the holding period, you likely have both ordinary income (the discount portion that should appear on your W-2) and capital gains/losses (any price movement from purchase to sale). Only the capital gains portion can be offset by your other investment losses. Since you have $11,000 in losses versus $8,400 in ESPP gains, you should be able to fully offset those gains and still have $2,600 in losses to carry forward or offset other gains. Just watch out for the wash sale rule if any of your losses involve the same company stock as your ESPP!

For those stuck on the insolvency worksheet, I found this real-world example helped me understand the big picture: Assets: Car worth $8,000 Checking account $1,200 Personal belongings $2,000 Total assets: $11,200 Liabilities: Credit card debt $13,000 Medical bills $5,000 Car loan $6,000 Total liabilities: $24,000 Insolvency amount: $12,800 ($24,000 - $11,200) If cancelled debt is $7,500, you can exclude the full amount. If cancelled debt is $15,000, you can only exclude $12,800. Hope this helps someone else!

Great breakdown of the insolvency calculation! One thing to add for anyone reading this - make sure you're valuing your assets at fair market value, not what you originally paid for them. For example, if you bought your car for $15,000 but it's only worth $8,000 now due to depreciation, use the $8,000 figure. Same goes for things like electronics or furniture - use what you could reasonably sell them for today, not what you paid. Also, don't forget about less obvious liabilities like unpaid taxes, student loans, or even money you owe to family members. Every dollar of legitimate debt counts toward proving your insolvency, so make sure you're including everything when you do your calculation.

Don't forget that worthless securities are still subject to the capital loss limitations. You can only offset up to $3,000 of ordinary income per year after you've used the losses to offset any capital gains. Had to learn this the hard way when I tried to claim $12,000 in losses from some penny stocks that went to zero in 2022. I offset about $2,500 in gains from other stocks, then could only use $3,000 against my regular income. The remaining $6,500 had to be carried forward to future tax years.

I went through this exact situation last year with some defunct crypto mining stocks that got delisted. Here's what worked for me: First, contact your broker's tax department (not regular customer service) and specifically request a "worthless securities letter" or "abandonment letter." Most major brokers have a standard process for this. If your broker won't cooperate, you can still claim the loss but need to document everything yourself. Save screenshots of your account showing the securities, any emails with your broker, and find public records of when the companies went bankrupt or were delisted. For the tax filing, you'll use Form 8949 and Schedule D. Mark the transaction with code "W" for worthless, use December 31st of the tax year as the "sale" date, $0 as the sale price, and your original cost basis as the loss amount. One important thing - make sure you're claiming these in the correct tax year. Securities become "worthless" when there's no reasonable hope of recovery, which is usually when the company files bankruptcy or is officially dissolved, not necessarily when they stop trading. Keep all your documentation for at least 7 years in case the IRS has questions. The key is being able to prove you actually owned the securities and that they truly became worthless during the tax year you're claiming.

I used FreeTaxUSA for the first time last year and had a pretty frustrating experience with their import feature. It completely failed to import my previous year's return from TurboTax, so I had to manually enter everything from scratch. This was especially annoying for carryover items like capital loss carryforwards. The software also didn't catch that I was eligible for the Earned Income Tax Credit until I specifically went looking for it. Other tax software I've used in the past would automatically suggest credits you might qualify for, but FreeTaxUSA seems to rely more on you knowing what to look for. That said, once I got everything entered correctly, the actual filing process was smooth and my refund came through without issues. Just be prepared to do more legwork yourself compared to the hand-holding you get with more expensive options.

I used FreeTaxUSA for the first time this past tax season and ran into a pretty specific but annoying issue. The software had trouble handling my HSA contributions correctly when I had both employer and personal contributions in the same year. It kept double-counting one of them, which would have led to an incorrect deduction. I caught the error during my final review, but it took quite a bit of digging through the forms to figure out where the problem was occurring. Their help documentation on HSA reporting was pretty sparse compared to other topics. Eventually got it sorted out, but it made me nervous about what other edge cases might not be handled well. The price is definitely right, and for straightforward tax situations it seems solid. But if you have any slightly unusual circumstances, just make sure to double-check everything carefully before filing. The software doesn't always catch calculation errors that might seem obvious.