Dear MontereyJill,
It sounds like the problem you have here may be related to the type and extent of salting. Although you did not detail the salting procedure, I will include a bit of theory here.
Salting not only removes whey to lower the moisture content, it also removes a great deal of lactose in the process. Residual lactose is fermented to give a sour flavor. In addition, salting inhibits the starter from fermenting the residual lactose while the cheese is in the press. The result is a drier cheese with a moderate acidity. Failure to salt properly results in the opposite effect.
Other confounding factors may play a role. If the mill size is too large, the whey removal and starter inhibition will not be as efficient. Also, if an inefficiently salted curd is pressed, no matter what the moisture content is or how long it is pressed, eventually, the curd granules will fuse and drainage will greatly decrease as the excess whey does not have an easy escape route. This may be exacerbated if the initial pressing weight is high; the soft and wet curd granules deform under the weight and fill in the spaces between unfused curds where whey would have escaped if the weight were less.
Although recipes are excellent, there is so much variability in cheesemaking that problems can occur, especially if you are not sure what to look for to ensure that the process is proceeding well. You will certainly develop this sense in time.
Kudos for taking on cheddar as your first cheese!
Happy cheesemaking,
UVM-cheese-LAB