I can imagine the “pressing disasters” you’ve had in the past, as I’ve had my share as well. So, give us the details: pressure, time, size etc. Your texture looks a bit open. You can help that some by warming the mold prior to pressing and keeping it warm during the first three cycles. But, as you say - the proof is in the eating, and with cheddar its usually quite a long wait for that.
Was this a traditional cheddar, or some shortened variety?