Has anyone successfully used the sales tax deduction calculator in previous years? I'm wondering if it's worth the effort or if I should just stick with my state income tax deduction.

I'm in a similar boat with itemizing for the first time this year! The IRS usually updates their calculators around December/January, so it's totally normal that 2024 isn't available yet. For now, you can get a rough estimate by using last year's calculator and adjusting for any major purchases you made in 2024. Since you mentioned big purchases with your new house, don't forget that you can also deduct sales tax on things like furniture, appliances, and even your car if you bought one this year - just keep all those receipts! The key is to compare your estimated sales tax deduction against your state income tax amount when you're ready to file. Whichever is higher is what you'll want to claim. Given that you're itemizing anyway for mortgage interest, it's definitely worth running both calculations to see which gives you the bigger deduction.

Thanks for all the helpful responses everyone! As someone who just started freelancing this year, this thread has been incredibly valuable. I was definitely overthinking the 1040-ES requirement - it sounds like I can just use the IRS Direct Pay system without worrying about submitting any forms. One follow-up question: If I'm using the safe harbor method (paying 100% of last year's tax liability), do I still need to use the 1040-ES worksheet to calculate my payments, or can I just take last year's total tax and divide by 4? My tax situation is pretty straightforward - just freelance income with standard business expenses. Also, does anyone know if there's a minimum income threshold where estimated payments become required? I've seen conflicting info about whether you need to pay if you'll owe less than $1,000.

Great question! I went through this same confusion when I started freelancing. The 1040-ES form is just a worksheet - you don't actually "file" it with the IRS. It's designed to help you calculate how much to pay each quarter. Here's what I learned: You can absolutely make your quarterly payments online without any paperwork. I use IRS Direct Pay (irs.gov/payments/direct-pay) - it's free, secure, and you just need your SSN and bank account info. When you make the payment, you'll select "Form 1040ES" as the form type and choose which quarter you're paying for. The key is keeping good records. Save your confirmation numbers and consider setting up an online account with the IRS so you can track your payment history. I keep a simple note in my phone with the confirmation numbers and dates - that's all the "filing" you really need for quarterly payments. Don't stress about not having a printer or avoiding tax prep services for this. The online payment system is actually much more convenient than mailing vouchers anyway!

One more resource that might help - if you remember the approximate dates you worked there, you can also try contacting your state's Department of Labor or Workforce Commission. They maintain records of employers in the state for unemployment insurance purposes, and these records typically include EINs. In Connecticut specifically, you'd want to reach out to the Connecticut Department of Labor. They might be able to provide the EIN if you can give them the company name, address, and approximate timeframe of your employment. Also, if the company had any professional licenses or certifications relevant to their industry, those are often searchable through state licensing boards and sometimes include EIN information in the public records. The combination of checking your 401(k) account (as mentioned above) and doing a quick Google search for the company name + EIN seems to work for most people before having to go the official transcript route.

Based on my experience dealing with similar situations, I'd recommend starting with the fastest options first before moving to the more time-consuming methods: 1. **Check your 401(k) or retirement account** - As StarStrider mentioned, this is often the quickest win. Log into any old retirement accounts from that employer. 2. **Search your email** - Look for any automated payroll emails, benefits enrollment confirmations, or tax document notifications. These sometimes contain EINs in the fine print. 3. **Contact your tax preparer** - If you used a professional tax preparer during those years, they often keep copies of all documents including W-2s with the EIN. 4. **IRS Wage and Income Transcript** - This is your most reliable backup plan. It's free and will definitely have the information, though it takes a bit longer. The key is to exhaust the quick options first since you're dealing with back taxes and probably want to get this resolved as soon as possible. I've found that most people can locate their EIN through one of the first three methods without having to wait for official transcripts. Also, once you do find it, make sure to save it somewhere secure along with other important tax information for future reference!

Just wanted to share my experience as someone who's been on an installment plan for over 3 years now. The CP89 statements are definitely helpful when they arrive in January/February, but I've found that setting up the online account at irs.gov is absolutely worth the initial hassle. Yes, the setup process can be frustrating (took me three attempts), but once you're in, you can track everything in real-time. One thing I haven't seen mentioned yet - if you're making extra payments beyond your required monthly amount to pay down the balance faster, those show up immediately in the online account but might not be as clear on the annual CP89 statement. The online system breaks down exactly how much of each payment goes toward principal vs. interest and penalties, which is super helpful for planning. Also seconding the advice about keeping bank records. I actually scan and save mine digitally along with screenshots from my online IRS account each month. Takes 2 minutes but gives me complete peace of mind that I have documentation of every transaction.

This thread has been incredibly helpful! I've been on an installment plan for about 4 months now and was getting anxious about not receiving any kind of statement or confirmation beyond the initial setup paperwork. Reading about the CP89 notices coming in January/February puts my mind at ease - at least I know what to expect and when. I'm definitely going to try the automated phone line at 1-800-829-1040 that several people mentioned. The idea of getting a balance update in just a few minutes without dealing with hold times sounds amazing. I'm also taking everyone's advice about keeping detailed records. Starting this month, I'm going to save my bank statements and take monthly screenshots of my online account (once I finally get it set up properly). After hearing about payment discrepancies, it's clear that having your own documentation is crucial when dealing with the IRS. Thanks to everyone who shared their experiences - this is exactly the kind of real-world advice you can't find in the official IRS publications!

Thanks everyone for all the helpful responses! Based on what you've all shared, I think I figured out what happened. The DoorDash income definitely explains a big chunk of it - I had no idea about self-employment tax being so much higher. Plus looking at my W-2, I only had about $2,800 withheld for federal taxes from my main job, which seems low based on what Gabriel mentioned. I'm going to double-check my FreeTaxUSA entries to make sure I didn't miss anything, but it sounds like this might just be the reality of having mixed W-2 and 1099 income without planning ahead. Lesson learned for next year - I'll either set aside money quarterly or adjust my W-4 to have more withheld from my regular job to cover the gig work taxes. Really appreciate everyone taking the time to explain this stuff. Tax season is so confusing when you're just starting out!

Great thread everyone! As someone who's been through this exact situation, I wanted to add that FreeTaxUSA actually has a really helpful "Why do I owe?" feature that breaks down exactly where your tax liability is coming from. If you go back into your return, there should be a summary page that shows the breakdown between regular income tax and self-employment tax. Also, for anyone doing gig work going forward - consider opening a separate savings account and automatically transferring 25-30% of your gig earnings into it throughout the year. That way you're not hit with a surprise tax bill. I learned this the hard way after owing $1,800 my first year doing Uber on top of my regular job! The IRS also has a safe harbor rule - if you pay at least 100% of last year's tax liability through withholding and estimated payments, you won't owe penalties even if you end up owing more at filing time. Something to keep in mind for planning next year.