I've pondered this thought before too. I know some people that book a hotel room at high season and in a certain area because cost per point has great value, this is a stupid reason to book an award stay. I never let my points dictate where i stay or fly but rather let my desire do it and use the points to lessen the burden on my pocket. Obviously you want to maximize your value per point but that shouldn't be the ultimate factor.

I think the proper way to value should be a need based valuation factoring in the lost opportunity. Skymiles are a great example, most value them as Skypesos but I actually value my pesos more than the average FF member because of the open jaw and 120K redemption to Africa. Trying to come up with a standardized fixed value for each point is silly i think, everyone should have their own individual valuation based on their needs and desires.