Has anyone considered the home office deduction angle instead of medical? If you have a legitimate home office where you do therapy or medical management for your family member, some security costs might be deductible that way too.

Thank you all for this incredibly helpful discussion! As someone new to navigating medical expense deductions, I'm dealing with a similar situation where my elderly father with Alzheimer's needs additional security measures to prevent wandering incidents. From what I'm gathering here, the key seems to be: 1. Getting proper medical documentation that establishes necessity (not just convenience) 2. Understanding the 7.5% AGI threshold requirement 3. Keeping detailed records of all medical-related components vs general security features 4. Being prepared for potential IRS questions with comprehensive documentation I'm particularly interested in the services mentioned like taxr.ai for getting initial guidance on whether expenses qualify, and Claimyr for actually speaking with IRS representatives when you need official clarification. Has anyone had experience using both services, or would you recommend one over the other for different situations? Also wondering - for those who successfully claimed these deductions, did you work with a tax professional or handle it yourself? I'm trying to decide if the complexity warrants professional help or if the documentation process is straightforward enough to manage independently.

Has anyone successfully carried forward capital losses from worthless securities to future tax years? I'm in a similar situation with about $20k in losses, but my income isn't high enough to use all the losses in one year with that $3,000 annual limit.

For anyone dealing with worthless securities, definitely check if your broker has any documentation available before going elsewhere. I had a similar situation with Schwab and they actually had a "Corporate Actions" section in my account history that showed when companies were delisted or went bankrupt. One thing to be really careful about - the IRS is pretty strict about the "worthlessness" year. It's not when the stock price hits zero, but when it becomes legally worthless (like through bankruptcy or delisting). Sometimes there's a gap between when a stock stops trading and when it's officially worthless for tax purposes. Also, if you're planning to amend multiple years, do them in order starting with the earliest year. The IRS processes amendments sequentially and it can get messy if they receive them out of order.

When I filled out my insolvency worksheet, I took pictures of all my furniture and household items and asked a local thrift store manager to give me a rough estimate of what they would price them at. The IRS accepted this documentation when they questioned my values.

I went through this exact same process about two years ago with a 2017 debt cancellation. The IRS audit was stressful, but here's what I learned that might help: For household goods, I used a simple rule: whatever I could reasonably expect to get at a garage sale. For thrift store items, I valued them at about 25-50% of what I originally paid. The IRS examiner told me they're looking for reasonable estimates, not exact appraisals. Regarding missing records - I was able to recreate some utility bills by calling the companies directly. Even though it was years later, most kept basic account history that showed my average monthly payments during that period. For medical bills, I contacted my insurance company for explanation of benefits statements that showed what I owed. One thing that really helped was creating a simple spreadsheet with three columns: Asset/Liability, Value/Amount, and Notes explaining my reasoning. The IRS examiner appreciated the organized format and clear explanations. For your land contract situation, definitely include it as a mortgage liability. I had something similar and the IRS considered it a legitimate debt obligation since I was contractually bound to make payments. Don't stress too much about perfect accuracy - they understand records get lost over time. Just be reasonable and document your thought process.

PRO TIP: your transcript will tell you way more than WMR. Go pull those if you can access them

I feel your pain! Been in the exact same situation - filed in late January as Head of Household and got stuck with that same "delayed beyond normal timeframe" message for what felt like forever. The worst part is how vague they are about timelines. From my experience, the Head of Household status does seem to trigger extra reviews more often. They want to make sure you actually qualify (supporting a qualifying person, paying more than half the household costs, etc.). I ended up having to wait about 8 weeks total before it finally moved to "Refund Approved" and then got deposited within a few days after that. The key thing is that once you see that delay message, you're basically in a manual review queue. No amount of checking the app will speed it up unfortunately. I know it's frustrating but try to check maybe once a week instead of daily - it'll save your sanity and your phone battery! 😅 Hang in there, it will eventually process!

Something nobody's mentioned yet - be careful about how you structure your medical benefits with a C Corp. One major advantage is you can deduct 100% of medical insurance premiums for employees (including yourself as an employee-owner), but the setup has to be done correctly with a qualified plan. Unlike an S Corp where health insurance is typically a personal deduction, with a C Corp it can be a business expense if set up properly. We saved about $24k annually just by structuring our health benefits correctly after converting to a C Corp. Talk to a benefits specialist who understands corporate structures before just continuing whatever you did with your S Corps.

Don't forget about the tax implications for your retirement planning too! C Corps have different options than S Corps. With your S Corps, you were probably using SEP IRAs or Solo 401(k)s. With a C Corp, you can set up some really advantageous plans like Cash Balance Pension Plans alongside your 401(k). With your income level jumping to $900k, this could be HUGE. We put away almost $280k pre-tax annually for retirement through our C Corp structure. The testing requirements get complicated, but with proper setup, the tax advantages are massive. Definitely worth talking to a retirement specialist alongside your regular CPA.