Based on the W-9 they provided, you are not required to issue them a 1099-NEC. Payments made to a corporation (C-Corp or S-Corp) are exempt from 1099-NEC and 1099-MISC reporting. Since they checked "LLC" and "Tax Classification: S" on their W-9, they have explicitly identified themselves as an S-Corporation. Under IRS Instructions for Form 1099-MISC and 1099-NEC, the only exceptions to this "corporate exemption" are for medical services and payments to attorneys. Property management fees do not fall under those exceptions. You (the Trust) would only send them a 1099-NEC if they were a Sole Proprietor or a Single-Member LLC that is "disregarded" (not taxed as a corporation). Their S-Corp status voids this requirement.
However, the Property Manager must send the Trust a 1099-MISC (Box 1) reporting the rent they collected and passed on to you.
Since the properties are in an Irrevocable Trust, the Trust will file Form 1041. You will deduct the property management fees as a business expense on the Trust's tax return. You do not need a 1099-NEC to "prove" the deduction; your bank records and the management agreement are sufficient evidence for the IRS.
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