Does anyone know if we still need to physically tag converted assets with asset numbers like businesses do? My accountant mentioned something about this but it seems excessive for my small home office with converted personal items.

One thing to keep in mind is the mixed-use percentage if any of your converted items aren't used 100% for business. For example, if you're using that MacBook for both business and personal activities, you can only depreciate the business-use percentage of its FMV at conversion. Also, make sure to document the date you actually started using each item for business purposes - this is your "placed in service" date for depreciation. It doesn't have to be when you officially started your business, but rather when each specific item began being used for business activities. For QuickBooks setup, create your fixed asset accounts first, then enter each converted item at its FMV (not original cost) with the conversion date as the acquisition date. The software should handle the depreciation schedules automatically once you specify the asset class and recovery period for each item.

One thing no one has mentioned yet - if you don't meet any safe harbor and have to use Form 2210 to calculate penalties, you can use the "annualized income installment method" by completing Schedule AI of Form 2210. This is SUPER helpful if your income is extremely uneven throughout the year. For example, if you made 70% of your income in Q4, you'd naturally have a much larger Q4 estimated payment. The annualized method accounts for this. It's more work to complete the form, but it can save you from penalties if your income isn't earned evenly and you don't meet either safe harbor test.

This is such a helpful thread! I've been dealing with similar confusion about estimated taxes. One thing I'd add is that it's worth keeping detailed records of when you made each payment and the reasoning behind the amounts. I learned this the hard way when the IRS sent me a penalty notice even though I thought I was in the safe harbor. Turns out one of my payments had been processed late due to a bank issue, which threw off my quarterly timing. Having documentation of when I initiated the payment (versus when it was processed) helped me get the penalty reversed. For anyone using the uneven payment strategy, I'd recommend: 1. Keep records showing your income timing if it's irregular 2. Document when payments were made vs. processed 3. Calculate both safe harbor methods to see which one protects you better The peace of mind is worth the extra paperwork!

I just went through this exact same situation a few months ago when I needed old W-2s from a restaurant job for a background check. Here's what I learned from trying basically every method mentioned in this thread: The IRS Get Transcript service really is your best option, but here's a tip that saved me a lot of headaches - if the online identity verification keeps failing, try using different variations of your address format. The system is really picky about how addresses are entered. If you lived at "123 Main Street Apt 2B" try "123 Main St #2B" or just "123 Main Street" without the apartment number. For Shake Shack specifically, I actually had luck calling their corporate HR line directly. They were surprisingly helpful and told me they use ADP for payroll. I was then able to contact ADP's employee services line with my SSN and employment dates, and they provided me with a wage statement that had all the same info as a W-2. Also want to second what others said about checking old email accounts - I found a "Your W-2 is ready" notification email from 2016 that I had completely forgotten about. Even though the link was expired, it reminded me that my employer had used a specific online portal (Workday) where I was able to recover my login and download the document. The whole process took about 2 weeks but was way less stressful than I expected. Don't let the awkwardness with your old manager stop you - there are definitely multiple ways to get this done without that conversation!

I've been through this exact situation and wanted to add a few more tips that might help! One thing I discovered is that if you filed your taxes electronically in 2015, there's a good chance your tax software provider still has your data archived, even if you can't access your old account. I had lost access to my old TurboTax account (college email issue just like you!), but when I called their customer support with my SSN and some basic info from that tax year, they were able to help me recover the account. They have pretty robust identity verification procedures that don't rely solely on email access. Also wanted to mention that some credit unions and banks that offered tax prep services back then (like Navy Federal or USAA) sometimes still have copies on file for members. If you used any financial institution for tax prep in 2015, it's worth giving them a call. One more thing - if you're dealing with a time crunch, the IRS can expedite transcript requests in certain situations (like for loan applications or legal proceedings). There's usually a fee involved, but it can get you the documents in 1-2 weeks instead of the standard 3-4 weeks for mail requests. The combination of IRS transcripts plus checking with corporate HR for the payroll processor should definitely get you what you need without any awkward conversations with old managers. Good luck!

Just want to add a real-world data point. I run an S-Corp and tried skipping salary for 2 years while reinvesting everything. Got audited and ended up owing back payroll taxes, penalties, and interest on what the IRS determined a "reasonable salary" would have been. They basically looked at what similar professionals in my field made and said I should have been paying myself (and paying payroll taxes on) at least that amount. The audit was triggered because I was actively involved (filed as full-time on my corporate docs) but had zero W-2 wages. They said this was an immediate red flag. Cost me way more in the end than if I'd just taken a salary from the beginning.

I'm dealing with this exact same situation right now as a new S-Corp owner! Reading through all these responses has been super helpful, especially the real audit experience from Daniel. It sounds like the consensus is pretty clear - if you're actively working in the business, you need to pay yourself a reasonable salary regardless of distributions. What I'm taking away is that I need to start documenting everything now: my hours worked, what comparable positions pay in my industry/area, and my business financial situation. Even if I can't afford a full market-rate salary right now during my growth phase, having that documentation seems crucial for justifying whatever salary I do set. Has anyone found good resources for researching what "reasonable compensation" actually means for their specific role and industry? I'm trying to figure out if there are standard databases or surveys that the IRS typically references during audits.

I've been following this discussion and wanted to share something that might help others in similar situations. While we can't change the tax deductibility issues right now, there are a few practical things you can do to minimize the financial impact of jury duty: 1. Check if your county has a hardship exemption process. Many courts will excuse or postpone service if you can demonstrate significant financial hardship. 2. Ask about scheduling flexibility when you call in. Some courts allow you to request specific weeks that work better for your schedule. 3. If you're self-employed, consider whether the timing conflicts with your busy season and request a postponement to a slower period. 4. Keep detailed records of all costs anyway - mileage, parking, lost wages. Even though they're not currently deductible, tax laws do change and having documentation could be useful if legislation passes to make jury duty expenses deductible again. The system definitely needs reform, but in the meantime these strategies can help reduce the personal cost of fulfilling this civic duty. The parking reimbursement tip mentioned earlier is particularly valuable - definitely worth asking about even if they don't advertise it!

Just wanted to add another perspective as someone who works in payroll and has dealt with jury duty situations for employees. One thing that's often overlooked is that some employers have better jury duty policies than others, and it's worth checking your employee handbook or HR policies before you serve. Some companies will pay your full salary during jury duty and let you keep the jury pay (so you actually come out slightly ahead). Others will pay the difference between your daily wage and the jury compensation. A few progressive companies even cover mileage or parking as part of their civic duty support. If your employer has a restrictive policy, it might be worth having a conversation with HR about the financial hardship, especially for longer trials. Many companies are willing to work with employees on a case-by-case basis even if it's not their standard policy. Also, for those tracking business mileage for self-employment - make sure you're using the correct mileage rate for 2025. The IRS hasn't announced the rate yet, but it was 67 cents per mile for 2024. That business mileage deduction can really add up over the year and partially offset some of the jury duty financial burden, even if you can't deduct the jury duty miles specifically.