Maintaining order history when creating orders as admin
I was able to solve this issue:

RECAP

Problem: Keeping order history in situations where the admin creates orders on behalf of Customers.

Solution:
a) User profiles must exist for the customer profiles. If the admin is creating customer profiles, a Rule can be created to a create User Profile whenever a Customer Profile is saved. To do this, I created a field for Customer Profiles called "Username", and use that data to populate the name of the new User.

b) A script will need to be written to automatically associate ownership of the Customer Profile by the appropriate User Profile. I was unable to create a functioning Rule which doesn't use my own php code to handle this.

c) One more rule to change the data value of the Order before it is saved. Specifically, you want to change [commerce-order:owner] to the right value (which can also be supplied by my Customer Profile's "Username" field). You will need to ensure that your rule has a Condition of "entity has field -> username" or the appropriate token won't be available.

I hope this can be helpful to someone!