TL;DR: The 30-Second Summary
The 3 Golden Rules:
- Never Mix Funds: Have a dedicated business checking account. No exceptions.
- Digital First: Use an app (Dext/QuickBooks) to snap photos of receipts instantly.
- Register Early: You must register with the City of Portland (PRO) even if you make $0.
The “Must-Know” 2026 Deadlines:
| Date | Deadline / Action Item | Agency |
| Jan 15 | Q4 Estimated Tax Payment | IRS / Oregon |
| Jan 31 | File Form 1099-NEC (for Contractors) | IRS / State |
| Mar 16* | S-Corp & Partnership Returns | IRS / State |
| Mar 16* | Business Personal Property Return | County Assessor |
| Apr 15 | Individual Tax Return (Form 1040) | IRS / State |
| Apr 15 | Portland Business License Tax | City of Portland |
| Apr 15 | Arts Tax ($35) | City of Portland |
| Apr 15 | TriMet Self-Employment Tax | Oregon Dept. of Rev |
Running a business in Portland, Oregon, is playing the game on “Hard Mode.”
In most cities, you worry about the IRS. In Portland, you have to worry about the IRS, the State of Oregon, TriMet, Metro, Multnomah County, and the City of Portland Revenue Division.
If you miss one deadline, the letters start coming.
We built this checklist to be your “Command Center.” Whether you are a solo freelancer or running a full crew, print this out (or bookmark it). If you follow this rhythm, you will be audit-proof.
Phase 1: The One-Time Setup (Do This Immediately)
You cannot play the game if you aren’t on the roster. If you haven’t done these three things, stop reading and do them now.
- [ ] 1. Separate Your Finances: Open a dedicated Business Checking Account. Never mix personal groceries with business software subscriptions.
- [ ] 2. Register with the Secretary of State: Ensure your LLC or Assumed Business Name (ABN) is active on the Oregon Secretary of State website.
- [ ] 3. Register with the City of Portland: Even if you work from home! Go to Portland Revenue Online (PRO) and set up your Business Income Tax account.
- Reference: How to Register Your Business Step-by-Step
Phase 2: The Monthly Rhythm (Keep Your Sanity)
Bookkeeping is not a “once a year” event. It is a monthly discipline.
- [ ] 1. Capture Receipts Digitally: Don’t stuff receipts in your wallet. Use an app like Dext or the QuickBooks mobile app to snap a photo immediately.
- [ ] 2. Categorize Bank Feeds: Log into QuickBooks Online weekly. Match your expenses to the correct category (e.g., “Office Supplies,” “Meals,” “Subcontractors”).
- [ ] 3. Reconcile Your Accounts: This is the most important step. Ensure the balance in QuickBooks matches the actual balance in your bank account to the penny.
- [ ] 4. Review the P&L: Look at your Profit & Loss statement. Did you make money this month? If not, why?
Phase 3: Quarterly Compliance (The “Estimates”)
If you wait until April to pay your taxes, you will likely get hit with an “Underpayment Penalty.”
- [ ] 1. Pay Federal Estimated Taxes (IRS): Due April 15, June 15, Sept 15, and Jan 15.
- [ ] 2. Pay Oregon Estimated Taxes: Generally due on the same dates as Federal.
- [ ] 3. Check Metro SHS Liability: If you expect to owe more than $1,000 in Metro SHS tax (because you earn over $200k/year), you must make quarterly payments on the PRO portal.
- Reference: Guide to the Metro SHS Tax
- [ ] 4. File Payroll Reports (If you have employees): File Form OQ (Oregon Quarterly) and Federal 941s.
Phase 4: The Annual Gauntlet (2026 Deadlines)
Mark these dates in your calendar in RED.
January 2026
- [ ] Jan 31: 1099 Deadline. You must file Form 1099-NEC for any contractor you paid more than $600 in 2025. You must also mail a copy to the contractor.
March 2026
- [ ] March 16 (S-Corps & Partnerships): Since March 15 is a Sunday, your Federal (1120-S / 1065) and State tax returns are due.
- [ ] March 16 (Personal Property Tax): If your business owns taxable equipment (desks, computers, machinery), you must file a Business Personal Property Return with your County Assessor (Multnomah, Washington, or Clackamas).
- Note: Late filing penalty is 5% immediately.
April 2026
- [ ] April 15 (IRS & State): Individual Income Tax Returns (Form 1040) and C-Corp Returns are due.
- [ ] April 15 (City of Portland / Multnomah County): Your Business License Tax Return is due on PRO.
- Tip: Even if you are exempt (under $50k gross), you must file to claim the exemption.
- Reference: Am I Exempt from Portland Taxes?
- [ ] April 15 (Arts Tax): The $35 personal tax for all Portland residents.
- [ ] April 15 (TriMet Tax): The Self-Employment transit tax (filed with your Oregon return).
- Reference: The TriMet Self-Employment Tax Guide
Phase 5: The “Red Flag” Check
Before you close out your books for the year, ask these three questions. If the answer is “No,” you are at risk.
- Do I have a W-9 for every contractor? If you get audited and don’t have W-9s, the IRS can disallow your deduction for that labor.
- Did I mix personal expenses? If you bought groceries on the business card, categorize them as “Owner’s Draw,” not “Office Expense.”
- Is my Net Income accurate? If your books say you made $100,000 profit but your bank account is empty, you have a bookkeeping error (or a spending problem).
Get the Checklist “Done for You”
Does looking at this list give you anxiety? That is exactly why we started Bridgetown Bookkeeping.
Our job is to handle Phases 2, 3, and 4 for you. We manage the deadlines, reconcile the accounts, and flag the risks so you can focus on your business.
Bridgetown Bookkeeping 
Leave a comment