$20 for a pound of cheddar is a bit ridiculous
Typically, one gallon of milk will yield 1 pound of cheese (alpines excluded). So it would be closer to $10 per pound.
I have access to raw milk from three creameries in my local health food store. Two sell for $9.99/gallon and the third sells for $11.99/gallon. I can buy creamline milk at another retailer and it sells for around $3.69/half gallon, or around $7.40/gallon. A gallon of decent quality milk at my local supermarket sells for about $3.50/gallon.
It is a pleasure using either the raw or creamline separately, or mixed. The higher cost of the milk is offset by the improved quality of the final product. I spend a fair amount of time making, washing, rubbing, and tending to the cheeses I make. I want to stack the deck a little in my favor to ensure a superlative outcome to a cheese affinage that might stretch out beyond 12 months. There's a lot going on in aging cheese and I want to give it the best possible opportunity to succeed gloriously.