@Esin Seref Dibirdi 100% correct. This can all be expensed on the P&L.

@Esin Seref Dibirdi I know we answered this on the call, but the $2,500 is not an annual limit it is on an asset by asset basis. So any piece of equipment less than $2,500 in cost will be immediately expensed and anything greater than that needs to be added to the depreciation schedule and depreciated. However, the asset can be 100% bonus depreciated, so it has the same effect, but different reporting on the tax forms.

Hi @Jennifer Shear, I totally understand the confusion. IL is essentially creating a dual responsibility structure. Airbnb collects and remits; however, the host (you) are still required to file the returns. My advice would be to file the HOOT return and report the gross receipts and take a deduction and/or exclusion for the tax paid via Air bnb to eliminate any taxes due while still being in compliance with the filing requirements. You should not be double paying the taxes.

Hi @Brendan McElhaney, You are correct. Any sole proprietor, partnership or LLC not organized as a corporation needs to be issued a 1099 by January 31st of the year following the tax year. The IRS can potentially issue penalties for late filings or for not filing at all per 1099 required. This can open you up to Audit risk if the IRS decides to challenge your expenses. Moreover, the more dire scenario would be that the IRS would disallow those expenses to contractors that were not issued 1099s. Yes, you can still deduct the expenses through the business: however, if you ever are targeted for an audit then there would be risk involved.

Hi @Vikas Sharma, Here is our preferred partner regarding the cost seg study. It isn't something that can be done online, it requires an engineer to perform the analysis. Ivan Grobler Head of Sales RE Cost Seg M: 346.214.6539 E: [email protected]

Hi @Jackie and Chris Roberson, 1. Regarding the estimated payments - those are typically paid quarterly on 4/15/26, 6/15/26, 9/15/26 & 1/15/27 for the 2026 tax year. Another method would be to increase your withholding on your W-2 income via filling out the W-4 form and specifically line 4(c) - Additional withholdings. You can divide your remaining estimated taxes owed by the remaining pay periods in the year and put that amount on that line to have it automatically deducted as a form of an estimated payment 2. Paying 110% of the prior year's tax ensures you won't receive underpayment penalties. This is known as the Safe Harbor estimate. You could end up owing more or less based on income, however you will avoid the late payment penalty of .5% per month of original taxes owed. Be aware that the 1099 net income will be subject to the additional 15.3% self-employment tax if reported on a Schedule C. 3. Technically, estimated payments are not mandatory; however, if you don't make proper estimated payments to the IRS and/or States then you will be hit with late payment penalties along with interest. You can wait until you file, but there will be interest added. Making the 110% Safe Harbor payment protects you from the interest accrued from late payments. The key take away is that making 110% tax payments from your prior year will protect you from any late payment penalties and accrued interest. Not making the 110% Safe Harbor payment and not making quarterly payments will result in late payment penalties and interest.