Leasing your own land to raise pasture-based dairy cattle;
Done all the time. Have good contracts if you own the animals. Can hire a caretaker, too.
Milking at a remote location from your creamery
Licensing a cheese plant and a milk parlor are separate activities. You can milk and haul with the relevant permits.
Making aged raw milk cheese from that milk, which has been transported off-site to your creamery?
Not a problem, provided your plant is licensed and you follow FDA regs.