If you use the rule of thumb that a puppy can hold its bladder for one hour per month of age, it makes sense that your 6 month old puppy would need to go out after 6 hours in the crate. I think the one hour per month of age is a good guideline.
Cut him some slack and adjust your schedule to suit your puppy's urgent needs. You might consider setting an alarm to wake yourself up before the puppy gets too uncomfortable and starts disturbing your roommate. Of course, as the puppy gets older, you can adjust the alarm time to suit the age of the puppy.
It's not as difficult as having a baby, but don't forget that your puppy is still a baby and has needs that are different from an adult dog's needs.
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