Hi Jon. I would say that the cooking and cheddaring processes contribute a fair amount to the end product's moisture content.
It also looks from your photo that you vacuum-bagged it. That would contribute to moisture retention as opposed to either cloth-wrapping, cream-coating, or developing a natural rind.
Certainly using a lower fat milk would also lean towards a leaner, drier cheese.
14 days is pretty short affinage for a Cheddar. More maturity and depth of flavor comes from longer aging as the enzymes and chemical processes have time to work their magic.
-Boofer-