Contact IRS directly. Use Form 4852. File by deadline. Use last paystub for estimates. Keep all communication records. Document all contact attempts. Take screenshots of emails. This happened to me. IRS was helpful. Employer eventually sent W-2. Had to amend return. Minor inconvenience. Better than penalties.

This is frustrating but totally fixable! Since you've already tried the direct approach multiple times, here's what I'd do in order: 1. **Check online first** - Log into any employee portals (ADP, Workday, etc.) you might still have access to. Sometimes W-2s are available electronically even when physical copies aren't sent. 2. **Call the IRS** - Don't wait until after Feb 28th like some suggest. You can actually call them now at 800-829-1040 since it's already past the Jan 31 deadline. They'll contact your employer directly. 3. **File with Form 4852** - If you can't get your W-2 in time, use your last paystub to estimate wages and withholding on Form 4852. This is completely legitimate and won't flag you for audit. 4. **Document everything** - Keep records of all your communication attempts with the employer. The IRS may ask for this. The good news is your employer can face penalties for not providing your W-2 on time, so once the IRS contacts them, they usually get moving pretty quickly. Don't let their delay mess up your filing deadline!

Just to clarify something others haven't mentioned - when the bank rejects the deposit, you might see a temporary hold or pending transaction in your Where's My Refund status. This doesn't mean there's a problem with your return, just that the system is processing the rejection and converting to a paper check. The status will update again once the check is scheduled to be mailed.

I've been through this exact situation twice now (2021 and 2023) and can confirm what others are saying. The process is actually pretty streamlined once you understand it: The bank rejection happens within 1-3 business days of the IRS sending the deposit. Then it takes about 10-14 days for the IRS system to process the rejection and generate a paper check. The check itself takes another 7-10 days to arrive by mail. One thing I learned the hard way - if you use a tax prep service like H&R Block or TurboTax, they sometimes use temporary accounts for direct deposits, which can complicate things. But in your case with a regular investment account, it should be straightforward. The Where's My Refund tool will show "refund sent" when they attempt the direct deposit, then change to "check mailed" once they convert it. Don't panic if you see the first status for a week or so - that's normal processing time. Pro tip: Sign up for USPS Informed Delivery so you can see when the check is actually coming to your mailbox. Makes the waiting much less stressful!

This reminds me of the scheme some people try with buying their own mortgage through their LLC. It simply doesn't work because the IRS looks at the substance of transactions, not just their form. Here's a simpler solution for peace of mind: look into federal student loan protections. They already have income-driven repayment plans, deferment and forbearance options specifically designed for job loss scenarios. Private loans might have fewer protections, but even they typically offer hardship programs. Also worth noting - student loans have unique discharge limitations in bankruptcy compared to other debts. This special treatment might further complicate your plan.

This is a creative idea, but unfortunately it's not going to work for several reasons that others have touched on. As someone who's dealt with similar corporate structure questions, I can tell you the IRS is very good at spotting these kinds of arrangements. The biggest issue is that student loans - especially federal ones - have specific statutory restrictions on assignment and transfer. Your loan servicer literally cannot sell them to your LLC even if they wanted to. The loans are designed to stay with approved servicers who can handle the complex federal requirements. Even if you could somehow make this work legally, you'd be creating a nightmare for yourself tax-wise. Any forgiveness of debt by your LLC to yourself would be taxable income, and the IRS would scrutinize every aspect of this arrangement. Your instinct about wanting protection from job loss is totally understandable, but you'd be better served looking into existing protections like income-driven repayment plans, economic hardship deferment, or unemployment forbearance. These are legitimate options designed exactly for the scenario you're worried about, and they won't create tax complications. If you're really concerned about long-term job security, consider building up an emergency fund specifically for loan payments rather than trying to restructure the debt itself.

As a newcomer to rental property ownership, I really appreciate this detailed discussion! I'm actually in a very similar situation - just purchased a duplex and planning some renovations before my first tenant moves in. One question that hasn't been fully addressed: when you're doing multiple improvement projects in the same tax year, does the timing matter for depreciation purposes? For example, if I install new flooring in January but don't add the laundry facilities until November, do they both start depreciating from when I place them in service, or can I group them together somehow? Also, I'm curious about the practical side of tracking all these different depreciation schedules. It seems like it could get pretty complex keeping track of what's on 5-year vs 27.5-year schedules, especially as you accumulate more improvements over the years. Do most landlords use spreadsheets or is there software that makes this easier? The advice about getting a tax professional for the first year setup definitely resonates with me. Better to establish the foundation correctly from the beginning!

As someone new to rental property tax issues, this thread has been incredibly educational! I'm in a similar boat with a duplex and was making the same mistake of wanting to lump all my improvement expenses together. The distinction between repairs (immediate deduction) vs improvements (depreciation) seems like the key thing to get right. From reading all these responses, it sounds like the test is whether you're restoring to previous condition or actually making it better than before. One thing I'm still unclear on - if I replace old, worn-out flooring with identical new flooring, would that be considered a repair or improvement? It's not making the rental "better" per se, but it's also not just patching a small damaged area. Also really appreciate the tip about the de minimis safe harbor election for items under $2,500. That could save a lot of paperwork headaches for smaller purchases like blinds, light fixtures, etc. Definitely planning to find a tax professional who specializes in rental properties for my first year, then potentially use some of the software tools mentioned here for future years once I understand the basics better.

I wonder if a Donor-Advised Fund might help in your situation. Instead of donating directly to charities each year, you can contribute a larger amount to a DAF in a single tax year (getting the full deduction subject to AGI limits), then distribute the money to charities over several years. This is especially useful if you have a high-income year and want to "bunch" several years of charitable giving into one tax year to exceed the standard deduction threshold, then take the standard deduction in subsequent years.

For what it's worth, I went through a similar thought process last year when I owed about $12,000 in taxes. I was also hoping charitable donations could somehow eliminate my tax bill entirely, but after doing the research (and talking to my CPA), I learned it just doesn't work that way. What I ended up doing was spreading my charitable giving across multiple years using a strategy someone mentioned - bunching donations. In 2023, I made a large donation that pushed my itemized deductions well above the standard deduction. This year, I'm taking the standard deduction and making smaller charitable contributions. It's not as satisfying as the "pay charity instead of IRS" fantasy I had, but it does optimize the tax benefits over time. One thing that helped me was realizing that even though the tax savings aren't dollar-for-dollar, I'm still doing good while reducing my tax burden somewhat. The $8,500 you're considering donating would genuinely help hurricane victims while saving you roughly $2,000+ in taxes (depending on your exact bracket). That's still meaningful, even if it's not the full amount you were hoping for.