One option you might not have considered: a partial cash out. You could take out just enough to cover your highest interest debt and roll over the rest. This might keep you from bumping up too far in tax brackets while still addressing your immediate needs. Also, check if your new 457b plan allows for loans - some do, and that could be a way to access some money without the tax consequences of a full distribution.

Something nobody has mentioned yet - if you're switching to a state job, check if they have a pension buy-back program! Many state retirement systems allow you to "purchase service credits" using your 401k funds through a direct transfer. This increases your future pension without triggering ANY taxes or penalties. It's completely different from cashing out. When I switched to a state university job, I was able to transfer about $45k from my old 401k to buy 5 years of service credits, which increased my future pension by about $850/month. No taxes, no penalties, just a direct transfer to the state pension system.

Just to add another perspective here - I'm a tax preparer who works with a lot of transportation industry clients. The special rule for transportation workers is legitimate but often overlooked. If you're subject to DOT hours-of-service limits (which most commercial truck drivers are), you can still deduct meal expenses while away from home overnight. This is one of the few remaining employee business expenses that survived the Tax Cuts and Jobs Act changes. For 2024 (filing in 2025), you can claim 50% of the standard meal per diem rate for the locations you traveled to. Keep a log of your overnight locations and dates - you don't necessarily need every receipt if you use the per diem method. The current per diem rate for meals and incidentals in most US locations is $59 per day (so you can deduct $29.50 per day), but it's higher in high-cost areas. These deductions go on Form 2106 and flow to Schedule 1.

Is anyone using any particular app to track their locations and meals for this deduction? I'm a long-haul driver and trying to be better organized for next tax season.

A heads up from someone who works at a bank - if you're paying online through IRS Direct Pay, make sure you initiate the payment at least 3-5 business days before the deadline! The payment isn't considered "made" until it actually processes, not when you submit it. I've seen customers get hit with late fees because they initiated payment on April 15th thinking that was sufficient.

Just adding one more payment option - if you use tax software like TurboTax, H&R Block, etc., you can usually set up direct debit from your bank account when you e-file. This is super convenient since everything is handled in one step - your return is filed and payment is scheduled for whatever date you choose (up to the deadline). That's what I did last year when I unexpectedly owed about $1,900.

My two cents as someone who's owned an S-Corp for 7 years - ALWAYS go with the extension if your CPA recommends it. Here's why: 1. Your in-laws aren't tax professionals (I assume). Your CPA is. Trust the expert. 2. Rushing tax work = mistakes = potential audit flags 3. Extension filing is super common and not a red flag 4. You've already paid the franchise tax, so you're good there 5. Amended returns are a much bigger headache than extensions I've filed extensions 5 out of 7 years with zero issues. Just make sure any estimated taxes are paid on time to avoid penalties.

Has anyone calculated what the actual financial risk is with extending the statute of limitations? Like if you file 3 months late, does that really mean the IRS has 3 extra months to audit you beyond the normal 3 years?

One thing nobody's mentioned yet - many US banks are becoming increasingly difficult about opening accounts for foreign-owned LLCs, even with Stripe Atlas. They'll often request substantial documentation, in-person visits, or may simply refuse. I tried this route (Australian citizen, Wyoming LLC) and ended up using Mercury and Wise Business instead of traditional banks. Still had to get an EIN and file Form 5472 annually even though my LLC was just holding funds for international expenses, exactly as you're planning.

Just to add a different perspective - have you considered setting up the entity in a different jurisdiction altogether? Singapore, BVI, or even Estonia's e-residency program might offer similar benefits with potentially less reporting hassle than a US LLC. I went the US route initially but switched to Singapore after calculating the total compliance costs. The reporting requirements were simpler for my situation as a digital nomad with no physical presence anywhere.