Do you know if homeowner's insurance premiums are ever tax deductible? I think I prepaid 14 months at closing and wondering if any of that is deductible anywhere.

Unfortunately, homeowner's insurance premiums aren't tax deductible for personal residences. They're considered a personal expense rather than a deductible housing expense. The only exception would be if you use part of your home for business - then you might be able to deduct the business portion of your insurance. However, if you paid for mortgage insurance premiums (different from homeowner's insurance), those might be deductible depending on your income level and when you got your mortgage. The rules change frequently on mortgage insurance deductibility, so that's worth looking into for your specific situation.

In my experience, most lenders only issue a 1098 if the total interest for the year exceeds $600. If you closed in late December, the few days of interest probably didn't hit that threshold, so they might have just included it in next year's form. You can still deduct it in the correct year though, even without a separate 1098.

Can you explain more about this accountable plan thing? I've never heard of it but sounds like it might be useful for my situation. My LLC is taxed as an S-corp already.

An accountable plan is an arrangement that allows your business to reimburse you for business expenses without those reimbursements being counted as taxable income to you. For it to qualify, you need three key elements: a business connection for the expense, adequate accounting within a reasonable time period, and returning excess reimbursements. For vehicles specifically, you can set up a plan where your S-Corp reimburses you at the standard IRS mileage rate for documented business miles. This creates a deductible business expense for the company while providing you tax-free reimbursement. It's often more advantageous than trying to deduct lease payments directly, especially for mixed-use vehicles.

Thats what i do! way easier and no headaches about mixed use. I just keep track of business miles in an app and bill my LLC monthly. My accountant said its the cleanest way to do it for a small business owner.

This is really important! When I refinanced from 4.5% to 2.75% during the pandemic, my interest payments dropped significantly. Great for monthly cash flow, but suddenly my itemized deductions fell below the standard deduction threshold. Worth checking if this applies to OP's situation.

Do you know if there's any standard way the IRS expects these to be reported? I'm using tax software and it keeps asking for positive numbers and then a separate indication of gain/loss.

The IRS forms themselves typically have separate columns or boxes for gains and losses, so you'd enter positive numbers in either the gain or loss section as appropriate. Most tax software is designed to match this approach, asking you to enter the amount as a positive number and then specify whether it's a gain or loss through a dropdown menu or checkbox. This is actually more foolproof than using negative numbers, as it prevents accidental reversals that could occur if you forgot to include the negative sign.

Your accountant is likely mixing up different types of securities. Section 1256 contracts (which include regulated futures contracts) are generally NOT subject to wash sale rules. This is one of the tax advantages of trading futures versus stocks or options. Since futures are marked-to-market at year end and receive the 60/40 tax treatment, the wash sale restrictions that apply to stocks and securities don't apply. All gains and losses are recognized in the tax year they occur.

So what happens if the checks never get cashed? Do you have to add that back as income in the next year?

If checks never get cashed, it depends on your state's abandoned property laws and how long it's been. For tax purposes, if you determine a check will never be cashed (recipient lost it, company no longer exists, etc.), you should void the check in your accounting system. For the following year, this effectively increases your cash balance. It's not technically "income" - you're just reversing the previous expense. If it's material and from a prior year, you might need to file an amended return, but for small amounts many accountants just adjust it in the current year since Schedule L is informational only for most S-Corps.

Yes, use your QuickBooks cash balance for Line 1. QB is already handling those outstanding checks correctly for cash basis accounting. When you wrote the checks in QB, it reduced your book cash balance immediately, regardless of when they clear the bank. That's why when you reconcile in QB, your starting point is the bank statement balance, and then you check off cleared checks to reach your book balance. Your QB cash balance (the book balance) is the correct amount to report on Line 1.