That's probably not oil....probably Calcium Chloride. I've never heard of oil being use to fill tires...
Anyway, I jack the tractor up (jack under the drawbar bracket) so the rear tires are just off the floor...maybe a ¼" or so.
Then rotate the tire to be checked so the valve stem is in the 12 O'Clock position. My rear tires both rotate when I'm doing this, so make sure both wheels are not touching the floor or pavement.
If you don't have an air-liquid tire gage...this would be a good time to get one.
Anyway, check the pressure as above and you'll get a true reading without all the mess.