Thanks for the solid advice! For the quarterly taxes, is it just a flat 30% of income or does it vary based on what expenses I've had that quarter? Also, do most banks offer business accounts to sole proprietors or do I need an LLC first?

The quarterly tax amounts should ideally be based on your actual profit for that quarter (income minus expenses), but many contractors use a simplified approach of setting aside a percentage of gross income to make it more manageable. The 30% is just a rule of thumb - your actual percentage might be higher or lower depending on your state tax situation and deductions. Most banks absolutely offer business accounts to sole proprietors - you don't need an LLC first. You'll typically need your Social Security number and possibly a DBA ("doing business as") registration if you're operating under a business name that's not your personal name. I'd recommend shopping around as some banks offer free business checking while others charge monthly fees.

Can confirm this 100%. I broke my wrist in a bike accident last year and couldn't code for 8 weeks. No income coming in but rent and bills still due. The disability insurance I had grumbled at paying for? Saved me from emptying my emergency fund.

Can you explain what you mean by tax loss harvesting? I'm in a similar situation with about $8K in losses this year.

Tax loss harvesting means strategically selling investments that have declined in value to realize losses that can offset capital gains or up to $3,000 of ordinary income per year. Since you already have $8K in losses, you'll use $3K this year against ordinary income, then have $5K carrying forward. In future years, if you have investments that have appreciated significantly and you want to sell them, your carried-over losses will offset those gains, potentially reducing or eliminating the tax impact. Just be careful of the wash sale rule - don't buy substantially identical securities within 30 days before or after selling at a loss.

Learned this the hard way too. Does anyone know if turbotax carries this info forward correctly if you use them consecutive years?

That's a really good point about spreading it out. I think I'll do the 5 paycheck option since that would be way less disruptive to my monthly budget. Do you think I need to specifically ask HR about the state tax withholding or would they typically handle both?

Definitely ask HR specifically about state taxes. In my experience, some payroll systems don't automatically adjust state withholdings when federal is increased. Just tell them you want to make sure both federal AND state taxes are being withheld appropriately for the HRA payment. They should be able to handle that for you.

I don't think that's accurate. The taxes you pay are based on the tax year they're for, not when you pay them. So taxes for 2023 income always count toward 2023 SALT deduction regardless of when you actually pay them.

Good point! Also worth checking Box 16/17 for state withholding too. Lots of people forget about state taxes when considering amendments.

Thanks for the tip! I just double-checked the form and there's no withholding in Box 4 or any of the state boxes. It looks like they treated me as a pure independent contractor with no tax withholding. Since I already reported the full income amount and paid the appropriate taxes, I'm going to follow the advice here and not file an amendment. I was worried the IRS might send me some kind of automated notice about a "missing" 1099, but it sounds like their system will see I already included the income. That's a relief!

Actually depends on what the payment was for. 1099-MISC is still used for certain types of payments like rent, prizes, medical payments etc. 1099-NEC is specifically for nonemployee compensation (like independent contractor work). So it could be correct depending on what services OP provided.

Did your refund come faster or slower when you filed jointly vs separately? I've heard joint returns sometimes take longer to process.

Our refund actually came slightly faster when we filed jointly compared to previous years filing separately. We e-filed in early February and had our refund within 14 days, which was about a week faster than our experience with separate returns. I think what matters more for processing time is how early you file and whether your return has any complicated elements that might trigger extra review. In our case, a straightforward joint return with W-2 income and child tax credits was processed very efficiently.

Yes! TurboTax has a feature that lets you compare filing statuses. After you enter all your info, there's an option somewhere in the tax tools section called "Tax Scenarios" or something similar that shows the difference in refund/amount owed. I did this last year when deciding between joint and separate filing. It's not super detailed in explaining WHY one is better, but it does show you the dollar difference.

Thanks for the info! That sounds exactly like what I need. I don't need the deep explanation as long as I can see which option saves us more money. I'll look for that Tax Scenarios feature when I start our return this year.