When you create a Class, Appointment, or Course and set one-plus pricing for a specific membership, you will be able to purchase this on behalf of the customer and select the custom pricing you have set up for them based on their membership.
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If during the registration process you find that at the check-out section you're unable to see or select this one-plus price, this is most likely due to the fact that this Class, Appointment, or Membership is not included with their membership.

Here's an example:

If your customer has purchased a membership which allows Classes & Appointments, and you then create a course where you enable one-plus pricing for that membership, the customer (and yourself) will not be able to purchase the membership at the one-plus price you set, as Courses have are not included in their membership.

You would therefore need to go into:

Memberships
​➔ click on the membership in question
➔ click on Edit next to Usability
​➔ Applicable to*

If this membership has been set to be applicable to "classes & appointments", then you would not be able to select the one-plus rate when purchasing the course, but if you set this to "Classes, Appointments, and courses" then you will be able to select the discounted rate at checkout.
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Then, scroll down the list of classes and courses and make sure the course in question is ticked, along with the "Alternate pricing for courses" check-box beneath it, and click on Save.

The same would go for memberships which are set to only be applicable to Courses alone. If you set up a class with one-plus pricing for that membership and classes have not been enabled on that membership, you would need to go through this process in order to enable them.
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Now, you will be able to complete this purchase on the customer's behalf with the correct pricing.