Has anyone had success getting the failure-to-pay penalties abated when filing an amended return for a capital loss carryback? We're in a similar situation but our CFO is saying it's not worth pursuing because the penalties will still apply even if the tax is reduced.

I went through almost the exact same situation with our C corp last year. A few key points from my experience: 1. The 3-year deadline Noah mentioned is correct, but don't wait until the last minute. The IRS processing time for corporate amendments can be 6+ months. 2. Regarding penalties and interest - they will be recalculated from the original due date based on your reduced liability after the carryback. However, you'll still owe some penalties for the period you didn't pay, just on a smaller base amount. 3. One thing that helped us significantly was filing Form 1139 (Application for Tentative Refund) along with the 1120X. This can speed up getting at least a partial refund while they process the full amendment. 4. Document everything about your cash flow issues and the market conditions that caused both the original payment problem and the subsequent losses. This can help with penalty abatement requests. The whole process took about 8 months for us, but we recovered about 65% of our tax liability plus got partial penalty relief. Definitely worth pursuing given your timeline - you still have nearly a year before the deadline.

Great question! I've been dealing with this exact issue for the past few years with my rental properties. You can definitely deduct your umbrella insurance as a rental expense, but there are a few important things to keep in mind. First, if your umbrella policy covers both personal assets and rental properties (which is common), you'll need to allocate the premium. I typically use the property value method - if my rental properties represent 60% of the total insured value, then I deduct 60% of the premium on Schedule E. Second, make sure you keep good documentation of your allocation method. I create a simple spreadsheet each year showing the property values and calculation, just in case the IRS asks questions later. One tip from my experience: if you're managing multiple rental properties, consider having your insurance agent break down exactly what portion of the umbrella coverage applies to each property. This makes the allocation much cleaner and gives you better documentation for tax purposes. The $325 annual premium you mentioned is pretty reasonable for umbrella coverage, and even if you can only deduct a portion of it, every legitimate business expense helps reduce your taxable rental income!

This is such a timely question! I just went through this exact situation with my CPA last month. The good news is that umbrella insurance premiums are absolutely deductible for rental properties - it's considered a legitimate business expense under IRS guidelines. What I learned from my CPA is that the key documentation piece is showing the "business purpose" of the insurance. Since umbrella policies provide additional liability protection beyond your standard landlord insurance, they directly relate to protecting your rental business assets and income stream. For allocation, I use a method based on liability exposure rather than just property values. My insurance agent helped me understand that umbrella policies are really about protecting against lawsuits and claims, so I consider factors like rental income generated, number of tenants, and property types when determining the business vs. personal split. One thing to watch out for - make sure your umbrella policy actually covers rental activities. Some standard personal umbrella policies specifically exclude business activities, including rental properties. If yours has that exclusion, you might need a separate commercial umbrella policy to get the coverage AND the tax deduction. Keep copies of your policy declarations page and any correspondence with your agent about the business coverage. The IRS likes to see clear documentation that the insurance is genuinely for business protection, not just personal asset protection that happens to include some rental properties.

Quick question about the food part of business travel - if I'm attending a conference in Vegas, are all my meals 50% deductible or just dinners out? What about if the conference includes some meals as part of registration?

Great question! I've dealt with this exact situation multiple times as a consultant who travels frequently for client meetings and industry events. The "lavish and extravagant" standard is really about reasonableness within the context of your location and business needs. Your budget of $1300-1900 for a Vegas conference sounds very reasonable. The IRS isn't expecting you to stay at budget motels - they understand that business travelers need appropriate accommodations that allow them to be productive and represent their business professionally. A few practical tips from my experience: - Standard business hotels (Hilton, Marriott, etc.) are totally fine, even in Vegas - Keep all receipts and the conference materials/agenda - Take photos of your receipts as backup - Make brief notes about business sessions attended and key contacts made - If you do any personal activities (shows, gambling), keep those expenses completely separate The key is demonstrating legitimate business purpose. As long as your primary reason for the trip is the conference and your expenses are reasonable for a business traveler in that location, you should be fine. The IRS is more concerned with people trying to write off luxury vacations than legitimate business travel to conferences. Also remember that your conference registration fee is 100% deductible, while meals not included in the registration are 50% deductible.

Anyone know how the new 3.8% Net Investment Income Tax applies to S-Corps? I heard there were some changes coming in 2025 that might affect distributions...

Great question! The S-Corp strategy is definitely still viable in 2025, and with $145K in business income, you're right in the sweet spot where it typically makes financial sense. Here's my take: you'll likely want to set your salary somewhere in the $70K-$90K range (depending on your specific role and local market rates), which would still leave you with $55K-$75K in distributions that avoid self-employment taxes. That could save you roughly $8K-$11K annually in SE taxes alone. A few practical tips from someone who made this switch: - Start researching payroll services now (Gusto, ADP, etc.) - you'll need one - Document your salary decision thoroughly - save industry salary surveys, job postings, etc. - Factor in the extra costs: payroll service (~$500-600/year), additional tax prep fees (~$500-1000), and any state fees - Consider timing - you generally need to elect S-Corp status by March 15th for it to be effective for the current tax year Even with all the extra costs and complexity, most businesses in your income range see net savings of $5K-$10K annually. The break-even point is usually around $60K-$80K in business income, so you're well above that threshold. Just make sure to run the actual numbers for your situation before making the switch!

One thing nobody mentioned - if you rent through these Uber programs, track your charging costs separately too! Sometimes they give you free Supercharger access, but sometimes not. If you pay for charging, those costs are deductible too, just like gas would be. I rented a Model 3 last summer and saved all my charging receipts - added up to about $90/week in deductions my tax guy said I wouldn't have been able to claim otherwise.

Great question about mixing deduction methods! I went through this exact scenario two years ago when my personal car broke down mid-year and I switched to Uber's Tesla rental program. You're absolutely right that you can't use standard mileage for a rental vehicle - the IRS is very clear about that. But the good news is that the entire $340 weekly rental fee is indeed deductible as a business expense, assuming you're using the vehicle primarily for rideshare/delivery work. The key thing to remember is documentation. When you make the switch, create a clear cutoff date in your records. For the period with your personal vehicle, track your business miles and use the standard mileage rate (currently 65.5 cents per mile for 2023). Then from your rental start date forward, keep all rental receipts and track your business vs. personal use percentage. Also don't forget about the charging costs if your rental doesn't include free Supercharger access - those are deductible too! I kept a simple spreadsheet with charging receipts and it added up to decent additional deductions. One tip: if you're on the fence about timing, consider waiting until the start of a new quarter to make the switch. It makes the record-keeping cleaner and reduces any confusion if you get audited.