I would start with 1 crate when first teaching him to love the crate, but once he's gotten that down, you can easily transfer the value into a new crate. We've taught our dog that "go to bed" just means run to the nearest empty crate. It might help to first start with similar style crates before transitioning to a different style so she gets the idea that your "crate" command means any crate.
Also don't forget that the puppy's first crate should just be big enough for him to stand up and turn around. This will make potty training much easier.
An added bonus is that once your dog loves running to crates, you can use them in all kinds of training where you want to practice with your dog at a distance such as recalls.
Recommended viewing: Crate Games (There is a section on how to specifically use two crates to build value for something else.)