I appreciate seeing different perspectives on this issue, especially from the enrolled agent. As someone who's been wrestling with this exact question, I think the key takeaway is that the IRS really focuses on the primary purpose of the expense. What I'm gathering is that there might be a middle ground approach: instead of trying to deduct personal therapy sessions, perhaps we should focus on clearly deductible professional development like clinical supervision, consultation groups, or continuing education that specifically addresses therapeutic techniques and case management. For those who do choose to deduct portions of therapy costs, it seems like meticulous documentation is absolutely critical - and even then, you're taking on audit risk. The medical expense deduction route mentioned by @Camila Jordan actually sounds like a safer approach for self-employed therapists, especially if you're already paying significant out-of-pocket medical expenses. Has anyone looked into whether peer consultation groups or case consultation with other professionals might be a cleaner way to get similar professional benefits while having a clearer business purpose for tax deduction?

As a newer member of the tax community, I've been following this discussion with great interest since I'm also a mental health professional dealing with this exact dilemma. What strikes me most is how the conversation has evolved from the original question about personal therapy deductions to exploring much safer and clearer alternatives. The peer consultation group approach that @StarStrider mentioned really resonates with me - it seems to offer many of the professional benefits we're seeking while having an unambiguous business purpose. I'm curious about the documentation requirements for these peer consultation groups. Do you typically need formal agendas or meeting minutes to substantiate the business expense, or is a simple receipt sufficient? Also, for those who have been in these groups, have you found them as personally beneficial as individual therapy in terms of preventing burnout and processing difficult cases? It seems like building a comprehensive professional development plan that includes peer consultation, continuing education, and formal supervision might address both our professional growth needs and tax compliance concerns more effectively than trying to navigate the grey area of personal therapy deductions.

Be careful with some of the advice here! I had a rental vacant for 9 months last year and my accountant said I could only deduct a percentage of expenses based on the occupied vs vacant months (8/12 of annual expenses). Something about "not actively engaged in business" during those months. Anyone else been told this?

I went through this exact same situation with my rental duplex last year! Had one unit vacant for 5 months and was worried about deducting expenses. After doing a lot of research and talking to my CPA, I can confirm that HOA dues are absolutely deductible during vacancy periods as long as you're actively marketing the property for rent. The key is documentation - I kept a detailed log of all my rental activities during the vacancy: every Zillow listing renewal, Craigslist post, showing appointment, and even declined applications. I also took photos of any maintenance or improvements I did to make the property more rentable. One tip that helped me: I created a simple spreadsheet tracking all my marketing efforts with dates and screenshots. When I filed my taxes, I included this as backup documentation. My CPA said this level of detail really shows the IRS that you're serious about renting the property and not just trying to claim personal property expenses as business deductions. Don't let the vacancy stress you out too much from a tax perspective - it's a normal part of being a landlord and the IRS recognizes that!

I completely understand how overwhelming this feels, especially while you're navigating so many changes after your divorce. You're definitely not alone in being caught off guard by unemployment tax withholding! Yes, unemployment benefits are subject to both federal and state taxes in most states, which explains why your payment is lower than expected. Here's what you need to know: **Federal withholding**: This is optional at a flat 10% rate. You have to actively choose this - it's not automatic. You can request it through your state's unemployment portal or by submitting Form W-4V. **State withholding**: This varies dramatically by state. Some states don't tax unemployment at all, while others offer withholding options similar to federal rates (typically 5-10%). To adjust your withholding settings: 1. Log into your state's unemployment portal 2. Find "Tax Withholding" or "Tax Elections" in your account settings 3. Choose your preferred amounts for federal and state taxes 4. Save changes (usually effective with next payment) I know it's tough to see your weekly benefit reduced when you're already budgeting carefully, but I can't stress enough how much better it is to have taxes taken out now rather than face a massive tax bill next April. I've seen too many people get hit with $2,000+ bills they weren't prepared for. You're asking all the right questions and being proactive about your finances during this difficult transition. The setup process is usually pretty straightforward once you find the right section. Take it one step at a time - you've got this! 💪

I'm so sorry you're dealing with this during such a difficult time in your life. Going through a divorce and unemployment simultaneously is incredibly challenging, and it's completely understandable that you're feeling overwhelmed. Yes, unemployment benefits are subject to both federal and state taxes, which is why your payment seems lower than expected. Here's what you need to know: **Federal taxes**: You can elect to have 10% withheld automatically, but this is NOT done by default - you have to actively opt in through your state's unemployment portal or by filing Form W-4V. **State taxes**: This varies widely by state. Some states (like Texas, Florida, Nevada) don't tax unemployment benefits at all, while others have withholding options ranging from 5-10%. **To adjust your withholding**: 1. Log into your state's unemployment portal 2. Look for "Tax Withholding" or "Tax Elections" in your account settings 3. Select your preferences for both federal and state taxes 4. Save the changes - they typically take effect with your next payment I know it's hard to see your weekly benefit reduced when you're already trying to budget carefully on your own for the first time. But trust me, it's much better to have taxes taken out now than to get hit with a potentially huge tax bill next April when money might be even tighter. You're being smart by asking these questions now rather than ignoring it. The setup usually only takes a few minutes once you find the right section in your account. Take it one step at a time - you're handling so much right now, but you've got this! 💙

Based on the data points shared here, it looks like 6-8 business days is pretty standard for IRS paper check delivery. I just received mine yesterday - it was issued on April 12th according to my transcript and arrived April 22nd, so exactly 10 calendar days (7 business days). I'm in Florida for reference. One thing that helped me track it was that the check number actually appears on your transcript if you look closely at the codes - mine showed up as a reference number that I could cross-reference when it arrived. Given your April 18th issue date, I'd expect delivery by this Thursday or Friday at the latest. The USPS Informed Delivery suggestions from others are spot on - it definitely beats the daily mailbox anxiety! If it helps with your contingency planning, the IRS typically allows 4-6 weeks for a payment trace if the check doesn't show up, but in my experience most arrive well within the standard timeframe.

I can add another data point to help with your analysis! My 2024 refund check was issued on April 10th according to my transcript and arrived in my mailbox on April 17th - exactly 7 calendar days. I'm located in North Carolina for geographic reference. What I found interesting is that the delivery was remarkably consistent with the timeframes others have shared here, despite different locations across the country. Based on your April 18th issue date, you should realistically expect delivery between April 25th-May 1st. I'd strongly recommend the USPS Informed Delivery service that several others mentioned - it completely eliminated the daily mailbox anxiety for me since I could see exactly when it was coming. The key insight from my experience is that the IRS postal delivery system is actually quite reliable once you understand the typical 6-8 business day window. If you haven't received it by May 2nd (14 calendar days), that would be outside normal parameters and worth investigating further.

Don't forget about your state filings too! Depending on your state, you may need to file separate state tax returns for the S-Corp period as well. Some states automatically recognize the federal S-Corp election, while others require a separate state election.

Just went through this exact scenario last year! A few additional things to keep in mind that saved me from headaches: 1. **Estimated tax payments**: If you made estimated tax payments as an LLC during 2023, you'll need to figure out how to allocate those between your Schedule C and S-Corp portions. The IRS considers them made ratably throughout the year unless you can prove otherwise. 2. **Asset basis transfer**: When you elected S-Corp status, any business assets (equipment, inventory, etc.) transferred from the LLC to the S-Corp at their adjusted basis. Make sure you're tracking this correctly for depreciation purposes on both returns. 3. **Health insurance deduction**: If you were deducting health insurance premiums as self-employed health insurance on Schedule C, you can continue doing this on your personal return for the S-Corp period (since you'll be a >2% shareholder). But the mechanics change slightly. Definitely get that Form 7004 filed today if you haven't already! The automatic extension is your friend here and gives you time to sort through all these details properly.