Preparing for 1099 & 1098 Season: What Mortgage & Real Estate Firms Need to Know

If you work in mortgage, real estate, or property management, January doesn’t ease you into the new year—it starts with deadlines, filings, and compliance checks. One of the biggest?

1099 and 1098 season.

Whether you issue payments to contractors or collect mortgage interest, these filings must be accurate and submitted on time. A little preparation in December can prevent last-minute scrambles and reduce audit risk later.

Here’s everything your team should review before the calendar turns.

1. Confirm Your Vendor List & W-9s Are Up to Date

The most common 1099 delays happen because vendor information is incomplete or outdated.

✔ Make sure every contractor has a current W-9 on file

✔ Check legal names vs business names

✔ Verify Tax ID numbers

✔ Confirm mailing addresses

✔ Identify vendors who hit the $600 threshold

Tip: If you need last-minute W-9s, send a reminder now—vendors often disappear during the holidays.

2. Review 1099-Eligible Payments in QuickBooks

QuickBooks Online makes this step easier, but it still requires a manual check.

Here’s what to review:

• Payments categorized as contractor labor

• Payments made via check, ACH, or cash

• Non-1099 payments (credit card, PayPal, Venmo) — these should be excluded

• Vendor status toggled to “Track Payments for 1099”

A 5-minute vendor audit today can save you an hour in January.

3. Mortgage Firms: Prep Your 1098 Mortgage Interest Reporting

For mortgage brokers and lenders, 1098 preparation often gets overlooked until the filing deadline approaches.

Review:

• Borrower payment history

• Mortgage interest collected

• Loan payoffs

• Adjustments affecting interest totals

• Your LOS export — make sure it matches QuickBooks

A clean reconciliation now makes 1098s simple later.

4. Double-Check Employee vs Contractor Classifications

Misclassifying someone as a contractor when they should be an employee is one of the fastest ways to attract compliance issues.

Ask:

• Do you control their schedule?

• Do they work exclusively for you?

• Do they rely on your tools, systems, or training?

If the answer is “yes,” the IRS may consider them an employee—not a contractor.

5. Resolve Any Outstanding Reconciliation Issues

Before you prepare 1099s or 1098s, confirm:

✔ All bank accounts are fully reconciled✔ Escrow, trust, or client money accounts tie out✔ Vendor balances are accurate✔ Loan-level details match your general ledger✔ Any duplicated or miscategorized payments are corrected

If your books aren’t clean, the filings won’t be either.

6. Set Up Your January Filing Timeline Now

January is short and always busier than teams expect.

Here’s the timeline most firms follow:

• First week of January: finalize vendor and borrower information

• Mid-January: generate 1099/1098 drafts

• By January 28: complete internal review

• By January 31: submit filings + send recipient copies

The earlier you start, the smoother it goes.

7. Want January to Be Easier? Use a Year-End Documentation Packet

Many firms use a simple “year-end packet” to streamline January filings. It usually includes:

• Current W-9s

• Vendor list

• Borrower list (for 1098s)

• Reconciled bank statements

• Escrow reports

• Rent roll or pipeline reports

• Summary of payments to contractors

If you don’t have one, we can help you build one that fits your industry.

A smooth year-end starts long before December. A 15-minute discovery call can save you days of stress.

👉 Book a call: https://calendly.com/info-greenkeyaccounting

Final Thoughts

Preparing for 1099 and 1098 season doesn’t have to be stressful. With a clean vendor list, accurate reconciliations, and a clear January timeline, your filings will be accurate—and you’ll stay on the right side of regulators.

If you want help reviewing your QuickBooks setup or getting a head start on filings, we’re here to help.