Except for the risk of just not being able to have teen-older relations. Awesome is a Core Mod and should trump whatever things script mods like Woohooer attempt to unlock so there shouldn't be much risk there. But if Awesome is set to actually disallow such activities, not just react to them, I really don't think any other mod can override that.

The answer to the original question is that yes, if one is playing with AwesomeMod in place then Woohooer's or any other mechanism if successful to allow for teen-older romance will trigger Awesome's pedo bear response.