I just wanted to add another resource that helped me when I was in this exact situation last year - if you're still having trouble getting through to the Marketplace after trying all these great suggestions, you can also contact your local congressman's or senator's office. I know it sounds dramatic, but they have constituent services staff who specialize in helping with federal agency issues like this. I called my representative's office after weeks of getting nowhere with the Marketplace directly, and their staff person was able to get my 1095-A reissued within 3 business days. They have direct lines to supervisors at these agencies and can often cut through red tape that regular customer service can't handle. You just need to explain that you've been trying to get your required tax document for weeks/months and haven't been able to reach anyone who can help. They'll usually ask you to email them documentation of your attempts (like call logs or screenshots of hold times), and then they contact the agency on your behalf. Obviously try the Spanish language phone trick and other suggestions first since they're faster, but if you're really stuck and the deadline is approaching, don't overlook this option. Your elected representatives' offices deal with IRS and Marketplace issues constantly during tax season - it's literally part of their job to help constituents navigate federal bureaucracy.

As someone who works in healthcare administration, I wanted to add another angle that might help - if you're enrolled in a plan through your employer's benefits portal that connects to the Marketplace (some large employers offer this), you can also try contacting your HR department. They sometimes have direct contacts at the Marketplace or can access enrollment records that show your Marketplace Identifier. I've seen this work particularly well for people who enrolled through their company's benefits system but are technically on a Marketplace plan. Your HR team might have records of the enrollment that include the specific numbers you need, or they might be able to escalate your case through their business relationship with the Marketplace. Also, just wanted to echo what others have said about keeping detailed records of all your attempts. I've helped employees navigate this exact situation, and having documentation of your good faith efforts (call times, reference numbers, who you spoke with) can be really helpful if you need to work directly with the IRS later. The IRS generally works with taxpayers who can show they made reasonable attempts to get required documents. The Spanish language phone trick is brilliant - I'm definitely sharing that with anyone else who runs into this issue. It's crazy that such a simple workaround can save hours of frustration!

Has anyone tried Drake Tax Software for S-Corps? My CPA uses it and suggested I might want to try the prosumer version for my small S-Corp.

I've been filing S-Corp returns for my consulting business for about 3 years now and have tried most of the major software options. Here's what I wish someone had told me when I started: For your first year, I'd actually recommend starting with TurboTax Business despite the higher cost. Yes, it's more expensive, but the interview process is really thorough and educational. It explains WHY certain deductions apply to S-Corps and helps you understand the underlying concepts, not just fill out forms. Once you're comfortable with S-Corp tax concepts (probably by year 2 or 3), then switch to TaxAct to save money. I made that transition and it worked well because by then I understood what I was looking for. One critical tip regardless of software: make sure you're paying yourself a "reasonable salary" through payroll before taking distributions. This is the #1 mistake I see new S-Corp owners make, and it can trigger an audit. The software won't necessarily warn you about this ratio, so it's worth discussing with your tax advisor even if you're filing yourself. Also, keep detailed records of all business expenses throughout the year - don't wait until tax time to organize everything. Both TurboTax and TaxAct are only as good as the information you put into them.

The biggest thing to keep in mind is that the IRS has specific rules about when you can start claiming business expenses. Since your websites are offline and you're still in development mode, you're likely in what the IRS calls the "pre-opening" phase. For startup costs like yours, you generally can't deduct them until you actually begin business operations. However, once you do launch, you can elect to deduct up to $5,000 in startup costs in your first year of business (assuming your total startup costs don't exceed $50,000). My advice? Keep meticulous records of everything you're spending now - those receipts will be gold when you do launch. Consider getting an EIN from the IRS (it's free) and maybe register your business name if you haven't already. These steps help establish that you're serious about this being a business rather than a hobby. The silver lining is that when you do launch, you'll likely be able to claim most of those expenses right away rather than having to spread them over 15 years like some other startup costs.

I went through something similar with my e-commerce startup last year. The key distinction the IRS makes is between "investigatory costs" (researching whether to start a business) and actual "startup costs" (expenses to create the business). From what you've described - building websites, developing products - these sound like legitimate startup costs since you've clearly moved beyond just thinking about starting a business. The $650 you've spent should qualify for the startup cost election once you launch. One thing that helped me was creating a simple spreadsheet tracking not just the expenses, but also the business activities I was doing each month. This helped demonstrate to my tax preparer (and potentially the IRS) that I was actively working toward launching a real business, not just dabbling in a hobby. The fact that you're asking these questions and keeping receipts already puts you ahead of a lot of people! Just make sure when you do launch that you formally elect to deduct those startup costs on your first business tax return.

One additional consideration that hasn't been mentioned yet - if your LLC units are subject to vesting and the company hasn't sold yet, make sure you understand what happens if you leave the company before the liquidity event. Many LLC operating agreements have "bad leaver" provisions that could affect your tax treatment or even result in forfeiture of unvested units. Also, since you mentioned the units only vest upon sale or IPO, you'll want to confirm whether there are any interim valuation events that could trigger partial vesting or affect your basis calculation. Some agreements have provisions for secondary sales or tender offers that could complicate the tax picture. The 83(b) election protects you from ordinary income treatment at vesting, but it doesn't necessarily protect against forfeiture provisions in your grant agreement. Worth reviewing those terms with both a tax professional and potentially an employment attorney if there are significant amounts at stake.

This is a really comprehensive discussion! One aspect I'd add that might be relevant to your situation - make sure you understand how the LLC's depreciation recapture (if any) might affect your sale. Even though you filed an 83(b) election, if the LLC has been taking depreciation deductions on assets over the years, some portion of your gain could be subject to depreciation recapture at ordinary income rates rather than capital gains rates. This is separate from the Section 751 "hot assets" issue that was mentioned earlier, but can similarly convert what you expect to be capital gains into ordinary income. The LLC should provide this information when the sale occurs, but it's worth asking about proactively so there are no surprises. Also, given that you've held these for 9 years, you might want to consider whether any tax-loss harvesting opportunities in your portfolio could help offset the capital gains when you do sell. Since this sounds like it could be a significant gain, having a tax planning strategy in place before the sale completes could save you quite a bit in taxes.

Anna, I'm so sorry for your loss. This thread has covered so many important aspects of dealing with an inherited IRA that goes to an estate - it's really become a comprehensive guide for anyone facing this situation. One final thought I'd add: since you're early in this process and clearly being very thorough, consider creating a simple spreadsheet or document to track all the key dates, amounts, and requirements. Things like the date of death, the December 31, 2023 account balance, each monthly RMD amount and date, the remaining RMD calculation, and key deadlines. This will be invaluable when working with your tax professional and estate attorney, and will help ensure nothing falls through the cracks. Given all the moving pieces - probate requirements, RMD calculations, tax planning across different scenarios, beneficiary notifications - having everything organized in one place will save you time and reduce stress. You've shown incredible diligence in asking the right questions and seeking proper guidance. With the professional team you're assembling and all the excellent advice in this thread, you're well-positioned to handle this complex situation successfully. Your uncle would be proud of how thoughtfully you're managing his affairs during such a difficult time. Wishing you the best as you work through this process!

Anna, I'm so sorry for your loss. Reading through your situation and all the excellent advice in this thread, I wanted to add one more perspective as someone who works in retirement plan administration. Since your uncle was taking monthly RMDs rather than a single annual distribution, there's a good chance he had set up automatic monthly withdrawals with the custodian. If that's the case, you'll want to confirm whether the custodian calculated those monthly amounts correctly based on his life expectancy and account balance. Sometimes these automatic systems use outdated factors or don't adjust properly for market changes in the account value. Also, given that he was organized enough to set up a trust for his other assets, I'd suggest checking if he had worked with a fee-only financial planner or CPA in recent years. They often keep detailed notes about clients' retirement distribution strategies and might have documentation about his intentions for the IRA beneficiary - sometimes people discuss updating beneficiaries but never follow through with the paperwork. One last practical tip: when you meet with your tax professional, bring a complete copy of the will along with the IRA documentation. The interaction between how the will distributes assets and the tax implications of the IRA distribution can sometimes create planning opportunities that aren't immediately obvious. You're handling this with remarkable thoroughness during what I know is an incredibly difficult time. The professional guidance you're seeking combined with all the insights shared here should help you navigate this successfully.