Don't forget quarterly estimated tax payments if you go 1099! That was my biggest shock when I switched to contracting. You have to basically be your own payroll department and send estimated payments 4x per year or face penalties. It's not just about which option nets more money but also the administrative overhead.

Another consideration that might tip the scales: as a 1099 contractor, you'll have much more flexibility with retirement contributions. You can potentially contribute up to $69,000 annually to a Solo 401(k) (for 2024), which is way more than the typical $23,000 employee limit plus that 3% employer match you'd get as a W2. If you're disciplined about maxing out retirement savings, the tax deferral benefits of a Solo 401(k) could be massive. You could potentially reduce your taxable income significantly more than you'd lose by giving up the employer match. Plus, you get to control your investment options completely instead of being limited to whatever plan the employer offers. The key is actually doing it though - it requires more self-discipline than having automatic payroll deductions, but the potential upside is substantial if you're already a good saver.

If you're a solo owner, don't forget about health insurance! Your S-Corp can reimburse you for health insurance premiums, which creates a business deduction for the S-Corp and isn't subject to FICA taxes. Just make sure it's set up correctly - the S-Corp should reimburse you after you pay personally, and it needs to be documented properly with a formal plan.

One thing I haven't seen mentioned yet is business meals and entertainment - if you've been meeting with clients or potential customers throughout the year, make sure you're capturing those expenses. For 2024, business meals are still 50% deductible if they're directly related to your business. Also, don't overlook professional services you might have used - legal fees, consulting, marketing services, etc. Even subscriptions to industry publications or software you use for business can add up. With your $145k revenue, you might also want to look into whether you can shift some income to next year if you have any outstanding invoices you haven't sent yet, or consider prepaying some 2025 business expenses before you file. Just make sure everything is legitimate and properly documented! Time is tight but these smaller deductions can really add up when you're dealing with a six-figure S-Corp income.

I've been dealing with similar EIN applications for complex entity structures in my accounting practice, and I want to add a few practical points that might help streamline your process: **Document preparation tip:** Before filling out Form SS-4, gather all the relevant documents (trust agreements, LLC operating agreements, etc.) and highlight the key sections that define ownership and trustee authorities. This makes it much easier to complete the form accurately and helps if the IRS asks for clarification later. **For the grantor trust LLC:** When using the online application, I've found success by being very concise in the explanation fields. Something like "Disregarded entity of grantor trust - grantor is tax owner" usually works well. The online system seems to handle shorter explanations better than lengthy ones. **Timing considerations:** If you need the EINs urgently for bank account opening, consider applying for the grantor trust LLC online first (since that's typically faster) while simultaneously mailing the paper application for the non-grantor trust LLC. This way you can start some of your banking setup while waiting for the second EIN. **Follow-up strategy:** When calling to check on paper applications, have your complete mailing details ready (date sent, certified mail tracking number, etc.). The IRS representatives can locate applications much faster with this information, and you'll get better service. One last suggestion - keep detailed notes throughout the process. These entity structures tend to come up again for amendments, additional entities, or tax questions, and having a clear record of exactly how you handled the initial EIN applications saves time later.

I just successfully completed this exact process for two LLCs with complex ownership structures, and I wanted to share what finally worked after several failed attempts. The key breakthrough was understanding that Form SS-4 has two completely separate requirements that often get confused: (1) the administrative "responsible party" requirement (must be an individual for IRS contact purposes), and (2) the actual tax ownership structure (determines how the entity is taxed). These don't have to be the same! **For your grantor trust LLC:** Since grantor trusts are tax-transparent, you (the grantor) are already considered the tax owner. List yourself as the responsible party in Part 3, then put the trust details in Part 7a. The online application actually works well for this scenario - just select "Other" for entity type and briefly explain "Disregarded entity of grantor trust." **For your non-grantor trust LLC:** Paper form is definitely the way to go. List an authorized trustee as the responsible party in Part 3, trust info in Part 7a, and in Part 9 add a simple explanation like "LLC owned by [Trust Name] and will be treated as disregarded entity for tax purposes." Pro tips that saved me time: Use certified mail for paper applications, call the Business & Specialty Tax Line (800-829-4933) after 2-3 weeks to confirm receipt, and keep copies of everything since they sometimes ask for clarification during processing. The whole process took about 3 weeks for my paper application and 10 days for the online one. Don't let the confusing instructions discourage you - once you understand what they're actually asking for, it's much more straightforward than it appears!

I switched from TurboTax to FreeTaxUSA two years ago and it's been great. The interface is definitely more basic but honestly that's kind of refreshing - no constant upselling or confusing premium features being pushed on you. For your situation with W-2s and basic investments, FreeTaxUSA will handle everything you need. I import my 1099-DIV and 1099-INT forms directly and it calculates everything automatically. The state filing fee is usually around $12-15 depending on your state, but federal is completely free regardless of complexity. One thing I really appreciate is their customer support - when I had a question about reporting some stock sales, I got a helpful response within a day via email. No trying to upsell me to a premium tier just to get basic help. The transition was easier than expected too. I just kept my previous year's TurboTax PDF handy for reference when entering carry-over information like estimated tax payments.

I made the switch from TurboTax to FreeTaxUSA last year and couldn't be happier with the decision. Like you, I was fed up with Intuit's corporate practices and the constant upselling throughout the filing process. FreeTaxUSA has been fantastic for my situation (W-2, investment accounts, standard deductions). The interface is clean and straightforward - no flashy graphics or unnecessary features, just gets the job done efficiently. Federal filing is truly free regardless of complexity, and state filing was only $14.99 for me. What really sold me was the transparency. No hidden fees, no bait-and-switch tactics, and no pressure to upgrade to premium tiers. When I imported my 1099-DIV and 1099-INT forms, everything calculated correctly without any issues. The only minor downside is that you'll need to manually enter your previous year's information since you can't directly import from TurboTax, but honestly it only took me about 20 extra minutes and gave me a chance to review everything more carefully. Their customer support has been solid too - I had a question about reporting some dividend reinvestments and got a helpful, detailed response via email within 24 hours during tax season. I'd definitely recommend giving FreeTaxUSA a try for the 2025 tax season!

i swear the irs website is held together with duct tape and prayers lololol

Update: just tried again and it's working now! Seems like the maintenance window is over. For anyone still having issues, try incognito/private browsing mode - sometimes cached login tokens can cause problems even after clearing cookies.