Finally got matched
So it looks like I screwed up my match by sending something that matched to Wyndham Platinum before reading The DDMS post. When trying to match again I was told that it's one match per year.
Then I asked it's by calendar year and the was their reply
"Thank you for contacting Wyndham Rewards Platinum.
As of 01/01/2019, you will be able to request another status match provided you do not earn the subsequent Member Level based on your stays with Wyndham Rewards."