Did you file the original 6 year old return electronically or on paper? If on paper, I'd recommend calling the IRS to confirm they've fully processed it before filing an amendment. In my experience, if you file an amendment too soon after a paper return, things can get really messed up in their system.

Just went through something very similar! Filed a 2018 return late last year and then realized I'd forgotten about estimated payments I'd made. The good news is you can definitely still amend since you just filed the original return. One thing I learned the hard way - make sure you have solid documentation of those estimated payments before you amend. I thought I remembered making four quarterly payments but when I dug through my old bank records, I'd only made three. The IRS will want to see proof like canceled checks or bank statements showing the payments went to the Treasury. Also, don't stress too much about the timing. Since you just filed the original return, you have plenty of time to get the amendment right. Take a few weeks to gather all your documentation and double-check everything before sending in the 1040-X. Better to be thorough than to have to amend your amendment!

Pro tip: get your congressman involved. Worked for me after my 3rd letter

Ugh, I feel your pain! I'm on my third 60-day letter for 2022 too. What's really annoying is they keep asking for the same documents I already sent. I started keeping copies of everything with delivery confirmations just to prove I sent stuff. The whole system feels broken honestly. Have you tried getting your account transcript online? Sometimes that shows what specific issue they're actually reviewing.

Don't overthink this. I've done Form 4852 twice for jobs that never sent W-2s. Just be reasonable with your estimates. The IRS mainly wants to see that you're reporting the income, not hiding it. For Fed withholding, I'd take what shows on bank deposits, add about 22% for taxes and withholdings to get gross, then figure about 12-15% of gross for fed withholding unless you're high income.

I went through this exact same situation two years ago! Here are a few additional tips that helped me: 1. Request a wage and income transcript directly from the IRS online at irs.gov. If your employer filed your W-2 electronically, it might show up there even if you never received the physical copy. This gives you the exact numbers instead of having to estimate. 2. Check your state's unemployment insurance website - sometimes they have wage records that can help you verify your quarterly earnings from that employer. 3. If you have any old email confirmations about direct deposits or pay notifications, those can help support your calculations. 4. Don't forget that if you had health insurance deductions, 401k contributions, or other pre-tax deductions, those need to be factored in when working backwards from your net pay to gross pay. The most important thing is to document everything you tried to do to get the actual W-2. Keep records of your attempts to contact the employer, any responses you got, and how you calculated your estimates. The IRS is generally understanding about these situations as long as you can show you made good faith efforts to get the correct information. Good luck with getting this sorted out!

Side note: Even if your CPA won't budge, YOU are the one signing your tax return, not them. The signature line says "Under penalties of perjury, I declare..." so ultimately it's your responsibility. If you have reasonable basis for your position (which it sounds like you do), you can override your CPA. They work for you, not the other way around. Either they file it the way you want with proper support, or you find someone who will. Just document your reasoning and keep support for your position in case of audit. Tax positions don't have to be 100% certain to be valid - they just need substantial authority.

Miguel, I completely understand your frustration! I went through something very similar last year with my beach condo rental. My CPA was also insisting on Schedule C treatment, but after doing my own research and getting a second opinion, I was able to demonstrate that Schedule E was the correct classification for my situation. The "substantial services" test is really the key here. From what you've described - providing furniture, parking, and basic essentials - that sounds more like typical rental property amenities rather than hotel-like services that would trigger Schedule C treatment. I'd strongly recommend getting that second opinion from a CPA who specializes in rental properties. Bring documentation of exactly what services you provide versus what you don't (no daily cleaning, no meals, no concierge services, etc.). The difference between paying SE tax and not paying it is significant enough to justify the cost of a consultation. Also keep in mind that if you do end up needing to switch CPAs over this issue, it's not necessarily a reflection on their overall competence - some practitioners are just more conservative or less familiar with the nuances of short-term rental taxation. The important thing is getting the classification right based on the actual facts of your situation.

In my experience as a homeowner in California, keep in mind that property tax in CA is typically much lower than other states due to Prop 13, but state income tax is higher. With your numbers, itemizing is clearly better ($37,500 mortgage interest alone is way over the standard deduction). For future tax planning, remember that mortgage interest is usually highest in the first few years of your loan and decreases over time. So while itemizing may be clearly beneficial now, in 10-15 years as your interest payments decrease, you may need to reevaluate. Also, don't forget about PMI if you're paying it - that's deductible too in most cases when you itemize!

Based on your numbers, itemizing is definitely the right choice for you! Your mortgage interest alone ($37,500) exceeds the standard deduction of $29,200. When you add in your charitable contributions ($1,850) and the capped SALT deduction of $10,000 (your $6,500 state income tax + $1,900 property tax), you're looking at total itemized deductions of around $49,350 - that's over $20,000 more than the standard deduction! One thing to double-check: make sure that $37,500 figure on your 1098 is actually deductible mortgage interest and not including any principal payments or other fees. Sometimes lenders include things like property tax payments made from escrow, which you'd count separately. Also, since you mentioned this is your first year as homeowners, don't forget to look into any first-time homebuyer credits you might be eligible for in California. Some local municipalities offer additional tax benefits that could further reduce your tax liability. The transition from standard deduction to itemizing can feel overwhelming at first, but with mortgage interest that high, you're clearly in itemizing territory for the foreseeable future. Just make sure to keep good records of all your deductible expenses throughout the year!