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You have to decide what is best for you.
I worry about your roommate making claims like you are his "ideal" woman. This is how I saw my current girlfriend when we began our relationship almost 8 months ago, but that view has changed slightly. I think if people enter a relationship assuming the other person to be some kind of "ideal", they will end up either altering their thinking and be understanding of their partner, or they will feel disappointed. You might want to think about how deep his need to challenge runs and how much he needs this ideal women.
You and your boyfriend have a long history and it sounds like he cares a lot about you. If there were ever a situation in your life that you honestly feel drained/depressed about, your boyfriend sounds like he would be there to help you, understand your situation, and display care.
In my opinion, if you know your roommate could not display the kind of caring and compassion required to accept you and be understanding should you ever fail to live up to his ideal women desire, then he is not worth it and there is nothing to debate about in your mind.
However, if you think he cares about you enough and could be accepting of you...Then the debate continues.
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