Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Start with the address and details about the rental.Create a section for tracking the lease information.

Does this strategy make sense, or am I overlooking any potential pitfalls?

I believe this model is archaic and motivates/unmotivates the wrong behaviors. 

I recommend checking out Multifamily Millionaire by Brandon Turner.

Ok, then know when in over your head and tap-out! 

However, I haven't been able to find any official information confirming whether this is legal or if it violates any laws.I'm hoping someone here might have experience with this or know of a reliable source that can clarify the legality of contacting a tenant's commanding officer.

This keeps it fair.

Do they use pen and paper to record this information or do they have some sort of software to manage it? 

A couple tips--Always best to house hack small multis when you are moving around from base to base.