Jar
Cheddar is salted, not brined, but you still don't want to over press it.
I personally flip just one time after 1-2 hours. With Cheddars, or any salted cheese, I start off with full pressure and do not gradually build up the weight like the recipe books call for. With unsalted (brined) cheeses, I start off with 50% of the final pressure, flip one time after 1-2 hours and increase to final pressure. As a small scale commercial producer, this is just a practical necessity. Otherwise I would be flipping cheeses until midnight every day. I try to finish up a batch by 4:00 p.m. every day and then it takes me over an hour to clean up and sanitize everything. So around 5:30 or so I flip once and go home around 6:00. I have to make cheese as my regular business allows, so there are lots of days when I get started making cheese late and I don't get out until 8:00 or 9:00. Long, but satisfying days.