You might want to look into whether your entity type is still right for you. As a single member LLC, you're probably filing Schedule C with your personal taxes. But if you're showing consistent losses, there could be other considerations. Have you talked to a tax pro about the potential benefits/drawbacks of S-Corp election? Might not make sense while you're still in the red, but something to consider if you think profitability is on the horizon.

I'm dealing with something very similar with my online reselling business - three years of losses and getting nervous about the hobby loss rule. One thing that helped me feel more confident was creating a formal business plan that shows specific steps I'm taking to become profitable. The key insight I got from my CPA is that the IRS isn't just counting years of losses - they're looking at whether you're operating like a real business. Since you have wholesale accounts, proper record keeping in QuickBooks, and are making operational changes, those are all strong indicators of business intent. For the inventory question if you dissolve - my understanding is that you'd need to report any inventory you keep at fair market value as income, but you should definitely confirm this with a tax professional. Have you considered maybe scaling back operations instead of fully dissolving? Sometimes reducing inventory investment while maintaining the business structure can help turn things around.

Has anyone tried applying for an advance from multiple tax prep companies? I got denied by H&R Block but wondering if I should try Jackson Hewitt or Liberty before just giving up on getting an advance this year.

Just want to point out that tax refund advances are basically payday loans with slightly better marketing. Even when you do get approved, there are usually fees hidden in the tax preparation costs. You're much better off just filing early and waiting the 2-3 weeks for the IRS to process your return. The advances made more sense years ago when refunds took 6-8 weeks, but now it's just not worth it.

Just a little tip I learned the hard way - if you change jobs mid-year after already hitting the OASDI maximum at your previous employer, your new employer will START WITHHOLDING OASDI AGAIN regardless of what you already paid! You'll get refunded the excess when you file your tax return, but it messes with your cash flow during the year. Happened to me last year and I had to wait months to get back like $3,000 in overpaid Social Security.

Unfortunately, there's no standard way to prevent this from happening. Each employer is required to withhold OASDI taxes independently based on the wages they pay you, regardless of what you've already contributed to other employers during the year. Your new employer's payroll system doesn't have access to information about your previous earnings or withholdings from other companies. Even if you provide documentation like W-2s or pay stubs showing you've already hit the cap, most payroll departments won't (or can't) adjust their withholding accordingly due to compliance and liability concerns. The good news is that you'll definitely get the excess back when you file your tax return - it's reported on Form 1040 as "Excess social security and tier 1 RRTA tax withheld." But yeah, it definitely creates a cash flow issue in the meantime. Some people plan for this by adjusting their tax withholdings or setting aside money if they know they're likely to switch jobs after hitting the OASDI cap.

Chiming in with actual IRS experience - I worked at a processing center for two years. ALL IRS locations are equipped to route mail to the correct destination. The PO Boxes are mainly for sorting efficiency, but mail gets rerouted internally all the time. Your amended return might be delayed by a week or so, but it definitely won't be rejected just because it went to Charlotte instead of Kansas City. The most important thing is that you used the correct form (1040-X) and included all required supporting documents. As long as you did that and the envelope was properly addressed to an actual IRS facility (which Charlotte is), you should be fine. The "Where's My Amended Return" tool likely won't show anything for 3-4 weeks regardless of which address you used.

Little tip from someone who's been audited twice - always keep copies of EVERYTHING you send to the IRS and always use certified mail with return receipt! That way you have proof of exactly when and where you sent it. For future reference, you can always double-check the correct mailing address on the IRS website rather than relying on tax software. Sometimes the software isn't updated for recent IRS address changes.

Something no one has mentioned yet is that you should also consider property taxes in your calculation. In expensive areas, property taxes can easily push you well over the standard deduction even without much mortgage interest. But then you hit the $10K SALT cap, which really reduces the benefit for high earners in high-tax states. I'm in NY with a $1.2M house, and my property tax alone is $20K, but I can only deduct $10K of it.

One thing I've found helpful as another high-income earner is to look at the effective interest rate after tax savings, not just the dollar amount saved. If you're borrowing $1M at 6.2% and your effective rate after tax benefits is 5.1%, that's still a pretty high rate historically. Would you borrow money at 5.1% to invest elsewhere? That's essentially what you're doing when you choose a smaller down payment to "take advantage" of the mortgage interest deduction.