Just wondering what software your preparer used? I'm asking because some tax software won't even let you e-file as a paid preparer without entering a valid PTIN. So either they're paper filing (which is unusual these days), using consumer software and pretending they're not a paid preparer, or somehow bypassing verification systems.

This is actually a really important question that @Freya Andersen raised. When I had my returns done, they were definitely e-filed - I got the electronic confirmation and everything. But now that you mention it, I never really paid attention to what software they were using or how the process worked on their end. If the software requires a valid PTIN to e-file as a paid preparer, then either they somehow got around that requirement or they're filing under someone else's PTIN. Both scenarios are pretty concerning and suggest this might be more serious than just forgetting to renew their registration. I'm definitely going to ask them directly about this when I confront them about the PTIN issue. The fact that they've been able to e-file for years without a valid PTIN suggests there might be some deliberate deception going on rather than just an oversight.

I went through this exact same frustration last year! Your former employer is definitely confusing the processes. The W-4R is for taxable distributions, but a direct rollover isn't a distribution to you - it's a transfer between qualified plans. Here's what finally worked for me: I called my NEW 401k provider first and asked them to initiate the rollover from their end. They sent me their "incoming rollover" forms and handled all the communication with my old plan administrator. This completely bypassed my former employer's HR department, who honestly didn't seem to understand the difference between direct and indirect rollovers. The key phrase you want to use is "trustee-to-trustee transfer" - this is the technical term that plan administrators understand. Also, make sure you have your new plan's acceptance letter or documentation showing they'll accept the rollover. If you're still getting pushback, you can reference IRS Code Section 401(a)(31), which specifically gives participants the right to elect direct rollovers. Good luck!

I'm dealing with almost the exact same situation right now! My former employer's HR department keeps insisting I need to fill out tax withholding forms even though I've explicitly requested a direct rollover multiple times. What's been particularly frustrating is that they seem to think ANY money leaving the plan requires tax withholding, which shows they don't understand that direct rollovers are specifically exempt from the 20% mandatory withholding rule. I'm definitely going to try the approach of having my new 401k provider initiate the transfer - that sounds like it could bypass a lot of this confusion. Has anyone had success getting their former employer to admit they were wrong about requiring the W-4R, or do they usually just quietly process it correctly once you go through the right channels? Thanks for all the helpful suggestions in this thread - it's reassuring to know this is a common problem and not just my former company being difficult!

One thing nobody's mentioned yet - make sure your SMLLC actually qualifies for S-Corp status! You need to meet the requirements like having only allowable shareholders (individuals, certain trusts, estates), no more than 100 shareholders, only one class of stock, and not be an ineligible corporation. I've seen people go through this whole process only to find out their LLC wasn't eligible in the first place.

I'm going through a very similar situation right now! Filed as SMLLC for two years, just submitted my Form 2553 late election last month. What really helped me was getting clarity on the "reasonable cause" requirement - I focused on explaining how my business income had grown substantially and I only recently learned about the self-employment tax savings potential of S-Corp status through a tax seminar. One tip I learned: the IRS is generally more lenient if you can show the election makes sense for your current business situation rather than just saying you missed the deadline. Also, I requested an effective date of January 1st of this year (not retroactive) specifically to avoid the headache of amending previous returns. My accountant said this approach has a higher approval rate since it doesn't create extra work for the IRS processing center. Still waiting to hear back, but feeling more confident after reading everyone's experiences here. Good luck with yours!

Anyone recommend a good tax software that handles rental property sales well? I tried TurboTax last year and it totally messed up my depreciation recapture calculations.

I went through a similar situation last year and learned some hard lessons about capital gains planning. While you can't directly offset the gains from your sold property with improvements to other properties, there are still some strategies worth considering for your current situation. First, make sure you're properly accounting for all the capital improvements you made to the property you just sold - these should increase your basis and reduce your taxable gain. Things like major renovations, roof replacement, HVAC systems, etc. can all be added to your cost basis. For your other properties, those improvements you're planning ($7,800 for flooring, $9,200 for the deck) will still benefit you tax-wise through depreciation over time. Just make sure to keep detailed records and receipts for everything. One thing to consider: if you have other investments showing losses this year, you might be able to harvest some capital losses to offset your rental property gains. Also, depending on your income level, you might qualify for the 0% capital gains rate on a portion of your gain. The tax code around rental properties is complex, so it might be worth consulting with a tax professional who specializes in real estate to make sure you're not missing any legitimate strategies for your specific situation.

Don't forget about state filings too! Everyone's talking about the federal forms, but depending on your state, you might also need to file state versions of unemployment tax returns and wage reports. Many states have their own online portals for this. I learned this the hard way when I got hit with penalties for missing my state filings even though I did all the federal ones!

Great advice from everyone here! I just wanted to add one more resource that might help - the IRS website has a really helpful "Forms and Pubs" search where you can find the specific instructions for each form. For your situation specifically: The **Form 940 instructions** have a section on electronic filing options and penalty relief for reasonable cause. Since you made all your payments on time, you're in a much better position for penalty abatement. For the **W-2 late filing**, definitely include a letter explaining why you filed late when you submit through the SSA portal. The IRS considers things like "first-time filer," "family emergency," or "relied on professional who failed to file" as reasonable cause. One thing I haven't seen mentioned yet - make sure you also give yourself (the employee) a copy of the W-2 before you file your personal taxes. You'll need it for your 1040, and having everything consistent between your business and personal returns will save you headaches later. The electronic filing options people mentioned are definitely your best bet. Even if you end up paying some penalties, it's way better than that $675 quote!