Don't overthink this. I was in your EXACT situation in college. You're already a sole proprietorship by default. Just keep good records and use Schedule C when you file taxes. For your car: if client reimburses some miles but not all, track EVERYTHING with an app like MileIQ or Everlance. Deduct only non-reimbursed business miles. LLCs cost money to form + annual fees in most states. Usually not worth it for students unless you have liability concerns or plan to scale up significantly.

As someone who went through this exact situation during my graduate program, I'd echo what others have said about already being a sole proprietorship by default. The key is getting your recordkeeping system down now before tax season hits. One thing I wish I'd known earlier: you can also deduct a portion of your home expenses if you use part of your home regularly and exclusively for business (like a dedicated workspace for administrative tasks, client calls, etc.). Even as a student, if you have a corner of your room that's primarily used for your contractor work, that could qualify for the home office deduction. Also, don't forget about other potential deductions beyond mileage - things like professional development courses, business-related software subscriptions, phone bills (business portion), and even some of your internet costs if you use it for work. These smaller deductions can really add up. The quarterly estimated tax payments are crucial too. Since you're setting money aside already, make sure you're actually making the quarterly payments to avoid underpayment penalties. Many students miss this and get hit with extra fees even when they have the tax money saved.

Has anyone used the Weinberg or Zaritzky method for these calculations? I've heard those are more accurate for increasing payment CLATs than the standard IRS approach, especially when the grantor is under 60 and the payment increase rate exceeds 2%.

For anyone working through this calculation manually, I'd recommend setting up your spreadsheet with separate columns for: (1) Year, (2) Probability of survival to that year, (3) Payment amount for that year, (4) Present value factor using Section 7520 rate, and (5) Present value of expected payment. The key insight is that for each year X, you're calculating: [Survival Probability] × [Payment Amount] × [1/(1+Section 7520 rate)^X]. Your payment amount grows each year by your chosen escalation rate, so Year 2 payment = Year 1 × (1 + escalation rate), Year 3 = Year 1 × (1 + escalation rate)^2, etc. I found it helpful to extend the calculation out to at least age 100 for the grantor, even though the present values become tiny in later years. The sum of all these present values gives you the charitable lead interest, and subtracting that from your initial contribution gives you the remainder interest. One tip: double-check your mortality table - make sure you're using the correct table for the valuation date and that you're reading the survival probabilities correctly (some tables show death rates instead).

I just want to echo what several others have said about documentation being absolutely critical in these family rental situations. I learned this the hard way when I got a notice from the IRS about my rental property expenses a couple years ago. What I wish I had known from the beginning is that the IRS specifically looks for whether you're operating with a "profit motive" when determining if something is truly a rental business versus personal use. When you're charging family significantly below market rate (like your sister paying only utilities plus 30% of mortgage), it's really hard to argue you have a genuine profit motive. The good news is that treating it as personal use isn't necessarily bad - you just need to be clear about what that means for your taxes. You won't report her payments as income, but you also can't deduct things like depreciation, repairs, or insurance as rental expenses. You can still claim mortgage interest and property taxes on Schedule A if you itemize. One practical tip: if you haven't already, I'd suggest drafting some kind of simple agreement with your sister that documents the arrangement. Even if it's below market rate, having something in writing that shows the terms, payment responsibilities, etc. can be helpful if questions ever come up later. It doesn't change the tax treatment, but it shows you're treating it seriously rather than just informal cost-sharing.

I've been following this thread with great interest since I'm dealing with a very similar situation with my adult daughter living in my rental property. She pays about 50% of what I could get at market rate. One thing I haven't seen mentioned yet is the potential impact on your basis and depreciation if you ever decide to sell the property. When you treat a property as personal use (which sounds like the right classification for your situation), you can't claim depreciation deductions during those years. This actually preserves more of your basis for when you eventually sell, which could be beneficial from a capital gains perspective. Also, I'd recommend keeping records of what fair market rent would be each year, even if you're not charging it. This helps establish a clear record of your decision-making process and shows you're aware of the market value. I take screenshots of comparable rentals in my area every January and keep them in my tax files. The key insight that helped me was realizing that the IRS isn't trying to penalize family arrangements - they just want to make sure people aren't artificially creating rental losses to offset other income when the property is really being used for personal/family purposes. Once I understood that perspective, the rules made a lot more sense.

Anyone know if box spreads on SPX options still qualify for section 1256 treatment? I've been using them for pseudo-financing and I'm not sure if I should be checking any of these elections for tax purposes.

I've been dealing with Form 6781 for my options trading for the past few years, and I totally feel your pain about the desktop vs. online TurboTax issue. The desktop version definitely requires more manual work for section 1256 contracts. A few quick tips that might help: 1. Double-check that your SPX and VIX options are actually being treated as section 1256 contracts in the desktop version. Sometimes the import doesn't categorize them correctly and they end up on Form 8949 instead of Form 6781. 2. For the "Net section 1256 contracts loss election" - only select this if you had significant section 1256 gains in the previous 3 years that you want to offset. If you didn't have prior gains, this election won't benefit you and your losses will just carry forward normally. 3. The account description can be pretty straightforward. I usually put something like "Options Trading Account - [Broker Name]" and have never had issues with the IRS. 4. If you're really stuck, consider reaching out to a tax professional who specializes in trading taxes. The cost might be worth it for the peace of mind, especially if you're dealing with complex positions or significant amounts. The learning curve is definitely steep when switching from the online version, but once you get the hang of it, the desktop version does give you more control over how everything is categorized.

Has anyone used the actual expense method vs. standard mileage rate for a leased vehicle? I've heard conflicting advice about which is better.

Just wanted to share my experience as someone who made this exact decision last year. I'm also a sole proprietor with about 55% business use on my vehicle. After going through all the calculations (and talking to my CPA), I ended up purchasing instead of leasing, primarily because of the Section 179 deduction and bonus depreciation opportunities. For 2024, you can still deduct the full purchase price in year one for many vehicles under Section 179 (up to $1,220,000 limit), which created a significant immediate tax benefit for my business cash flow. One thing that really helped was keeping meticulous records from day one. I use a simple app to log every trip with the business purpose, and I photograph my odometer reading at the beginning and end of each tax year. The IRS loves detailed contemporaneous records if you ever get audited. Also, don't forget about the state tax implications - some states have different rules for vehicle deductions that might influence your decision. In my state, the sales tax on the purchase was also partially deductible as a business expense. The key is running the numbers for YOUR specific situation rather than relying on general advice. Vehicle cost, expected mileage, business use percentage, and your current tax bracket all factor into what's optimal.